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WO2005058860A1 - Procede pour produire un compose d'acide 4-(non)substitue tetrahydropyran-4-carboxylique ou un compose ester de celui-ci - Google Patents

Procede pour produire un compose d'acide 4-(non)substitue tetrahydropyran-4-carboxylique ou un compose ester de celui-ci Download PDF

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Publication number
WO2005058860A1
WO2005058860A1 PCT/JP2004/018942 JP2004018942W WO2005058860A1 WO 2005058860 A1 WO2005058860 A1 WO 2005058860A1 JP 2004018942 W JP2004018942 W JP 2004018942W WO 2005058860 A1 WO2005058860 A1 WO 2005058860A1
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formula
group
compound
reaction
substituted
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English (en)
Japanese (ja)
Inventor
Shigeyoshi Nishino
Kenji Hirotsu
Hidetaka Shima
Keiji Iwamoto
Takashi Harada
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Ube Corp
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Ube Industries Ltd
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Priority to JP2005516372A priority Critical patent/JP4867350B2/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Definitions

  • the present invention relates to a method for producing a 4-substituted or unsubstituted tetrahydropyran_4_carboxylic acid compound or an ester aldehyde compound thereof from a 4_substituted or unsubstituted 4-cyanotetrahydropyran compound, and a raw material compound thereof.
  • the present invention relates to a method for producing a certain 4-substituted or unsubstituted-4-cyanotetrahydropyran compound.
  • the 4-substituted or unsubstituted tetrahydropyran-4-carboxylic oxide compound or an ester compound thereof is a compound useful as a raw material for a pharmaceutical or an agricultural chemical or a synthetic intermediate.
  • tetrahydropyran_4_carboxylic acid is used in the presence of lithium diisopropylamide synthesized from diisopropylamine and n_butyllithium. And methyl iodide are reacted in a mixed solvent of hexane and tetrahydrofuran for 3.5 days to produce 4-methyltetrahydropyran_4_carboxylic acid (for example, see Patent Document 1).
  • tetrahydropyran-4,4-dicarboxylic acid is heated to 185 ° C to obtain an isolation yield of 64%.
  • a method for obtaining tetrahydropyran-4-carboxylic acid is known (for example, see Patent Document 2).
  • the above method is not satisfactory as an industrial method for producing a 4-unsubstituted tetrahydropyran-4-carboxylic acid compound which requires a high reaction temperature and has a low yield.
  • Patent Document 1 Japanese Patent Publication No. 2002-501066
  • Patent Document 2 International Publication WO03 106418
  • Patent Document 3 JP-A-2000-281672
  • Patent Document 4 JP-A-5-279319
  • the first object of the present invention is to provide a 4-substituted or unsubstituted-4-cyanotetrahydropyran compound under mild conditions that solves the above problems and requires no complicated operations.
  • 4-substituted or unsubstituted tetrahydropyran-4-carboxylic acid compound capable of producing a 4-substituted or unsubstituted tetrahydropyran-4-carboxylic acid compound or an ester compound thereof in a high yield from
  • Another object of the present invention is to provide a method for producing the ester compound.
  • a second object of the present invention is to solve the above problems, and to obtain 4-substituted or unsubstituted-4-cyanotetrahydridopyran compounds from 4-cyanotetrahydropyran compounds in high yield without requiring complicated operations.
  • a third object of the present invention is to solve the above problems, and to produce a 4-cyanotetrahydropyran compound from a 4-substituted tetrahydropyran compound in a high yield by a simple method.
  • An object of the present invention is to provide a method for producing a 4-cyanotetrahydropyrani conjugate.
  • the first invention of the present invention provides a compound of the formula (2) in the presence of an acid or a base:
  • R 1 represents a hydrogen atom or a hydrocarbon group
  • R 2 represents a hydrogen atom or a substituent having a hydrogen atom or a substituent
  • R 3 OH (3) wherein R 3 represents a hydrogen atom or a hydrocarbon group
  • R .C0 2 R 3 [0013] where: R 2 and R 3 are as defined above,
  • the second invention of the present invention provides a compound of the formula (4): Wherein R 1 is as defined above,
  • R 2 has the same meaning as described above, and X represents a leaving group.
  • the third invention of the present invention provides (6):
  • a method for producing a 4-cyanotetrahydropyrani conjugate represented by the formula (4) characterized by reacting a 4-substituted tetrahydropyran compound represented by the formula with a cyanating agent.
  • 4-substituted or unsubstituted tetrahydropyran can be produced in a high yield from a 4-substituted or unsubstituted-4-cyanotetrahydropyran compound under mild conditions without requiring complicated operations.
  • An industrially suitable method for producing a 4-substituted or unsubstituted tetrahydropyran-4-carboxylic acid compound or an ester compound thereof capable of producing a 4-carboxylic acid compound or an esterified compound thereof. I can do it.
  • 4-unsubstituted-4-cyanotetrahydrovilla without complicated operation An industrially suitable method for producing a 4-substituted-4-cyanotetrahydropyran compound, which is capable of producing a 4-substituted-4-cyanotetrahydropyran compound from a pyridine compound in high yield, can be provided. I can do it.
  • a 4-cyanotetrahydropyrani conjugate can be produced in a high yield from a 4-substituted tetrahydropyrani conjugate by a simple method. Providing a recipe can be provided.
  • R 1 is a hydrogen atom or a hydrocarbon group, and examples of the hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • R 2 is a hydrogen atom or a hydrocarbon group which may have a substituent, and the hydrocarbon group has the same meaning as that of R 1 .
  • These groups include various isomers.
  • the aforementioned hydrocarbon group for R 2 may have a substituent. Examples of the substituent include a substituent formed through a carbon atom, a substituent formed through an oxygen atom, a substituent formed through a nitrogen atom, a substituent formed through a sulfur atom, and a halogen atom.
  • Examples of the substituent formed through the carbon atom include an alkyl group such as a methyl group, an ethyl group, a propynole group, a butyl group, a pentyl group, and a hexyl group; a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group.
  • cycloalkyl groups such as cyclohexyl group and cyclobutyl group; alkenyl groups such as butyl group, arylinyl group, propenyl group, cyclopropenyl group, cyclobutyl group, cyclopentyl group; quinolyl group, pyridyl group, and pyrrolidyl group Heterocyclic groups such as phenyl, pyrrolyl, furyl and phenyl groups; aryl groups such as phenyl, tolyl, fluorophenyl, xylyl, biphenyl, naphthyl, anthryl and phenanthryl; acetyl, Propionyl group, atariloyl group, bivaloyl group, cyclohexylcal Acyl groups such as bonyl, benzoyl, naphthoyl and toluoyl groups (which may be acetalized); carboxy
  • Examples of the substituent formed via the oxygen atom include a hydroxyl group; a methoxyl group, an ethoxyl group, a propoxyl group, a butoxyl group, a pentyloxyl group, a hexyloxyl group, a heptyloxyl group, a benzyloxyl group and the like.
  • Examples of the substituent formed via the nitrogen atom include primary amino groups such as methylamino, ethylamino, butylamino, cyclohexylamino, phenylamino, and naphthylamino; dimethylamino, getylamino, Secondary amino groups such as dibutylamino group, methylethylamino group, methylbutylamino group, diphenylamino group, N-methyl-N-methanesulfonylamino group; morpholino group, piperidino group, piperazinyl group, virazolidinyl group, pyrrolidino group And heterocyclic amino groups such as indolyl groups; and imino groups. In addition, these groups include various isomers.
  • Examples of the substituent formed via the sulfur atom include a mercapto group; a thioalkoxyl group such as a thiomethoxyl group, a thioethoxyl group, and a thiopropoxyl group; a thiophenoxynole group, a thiotoluyloxyl group, and a thionaphthyl And a thioaryloxy group such as a xyl group. These groups include various isomers.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • Examples of the acid used in the reaction of the first invention include sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, formic acid, acetic acid, chloroacetic acid, Forces such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.
  • sulfuric acid, hydrochloric acid, and phosphoric acid are used. These acids may be used alone or in combination of two or more.
  • the base used in the reaction of the first invention for example, lithium hydroxide, hydroxyl Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate and potassium hydrogen carbonate Alkali metal bicarbonates; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; amines such as triethylamine and tributylamine; and pyridines such as pyridine and picoline S, preferably sodium hydroxide, hydroxide Potassium is used.
  • These bases may be used alone or in combination of two or more.
  • the amount of the acid and the base to be used is preferably 0.150 mol, more preferably 1.0-20 mol, per 1 mol of the 4-substituted or unsubstituted-4-cyanotetrahydropyrani conjugate. .
  • the reaction of the first invention is desirably performed in the presence of a solvent.
  • the solvent used is not particularly limited as long as it does not inhibit the reaction, and examples thereof include water; alcohols such as methanol, ethanol, isopropyl alcohol and t-butyl alcohol; and N-dimethylforma.
  • Amides such as amides, N, N-dimethylacetoamide, N-methylpyrrolidone; Ureas such as ⁇ , ⁇ '-dimethylimidazolidinone; Sulfoxides such as dimethyl sulfoxide; Getyl ether, diisopropyl ether, tetrahydrofuran, dioxane, etc.
  • Ethers aliphatic hydrocarbons such as hexane, heptane, and cyclohexane; halogenated hydrocarbons such as methylene chloride and dichloromethane; and aromatic hydrocarbons such as benzene, toluene, and xylene.
  • aliphatic hydrocarbons such as hexane, heptane, and cyclohexane
  • halogenated hydrocarbons such as methylene chloride and dichloromethane
  • aromatic hydrocarbons such as benzene, toluene, and xylene.
  • water and alcohols are used. These solvents may be used alone or in combination of two or more.
  • the amount of the solvent to be used is appropriately adjusted depending on the uniformity of the reaction and the stirring property. Preferably it is 0.1 20 ml.
  • R 3 is a hydrogen atom or a hydrocarbon group.
  • the hydrocarbon group include a carbon atom such as a methyl group, an ethyl group, a propyl group, and a butyl group.
  • An ethyl group is a hydrogen atom or a hydrocarbon group.
  • the hydrocarbon group include a carbon atom such as a methyl group, an ethyl group, a propyl group, and a butyl group.
  • a linear or branched alkyl group having 1 to 6 children an aralkyl group such as a benzyl group or a phenyl group
  • the amount of the water or alcohol used is preferably 1 to 100 mol, more preferably 2 to 20 mol, per 1 mol of the 4-substituted or unsubstituted-4-cyanotetrahydropyran compound.
  • the amount of the acid to be used is preferably 0.1 to 10 mol, more preferably 0.5 5.0 mol, per 1 mol of the 4-substituted or unsubstituted-4-cyanotetrahydropyran compound.
  • the reaction of the first invention is, for example, a reaction in which a 4_-substituted or unsubstituted-4-cyanotetrahydropyran compound, an acid or a base, water or an alcohol, and a solvent are mixed and stirred. It is performed by the method described above. At this time, the reaction temperature is preferably 0 200 ° C, more preferably 10 130 ° C, and the reaction pressure is not particularly limited.
  • the 4-substituted-4-cyanotetrahydropyran compound represented by the formula (2) used in the first invention can be prepared by reacting the compound of the formula (4):
  • R 1 is as defined above
  • R 2 has the same meaning as described above, and X represents a leaving group.
  • the second invention of the present invention facilitates production.
  • the 4-unsubstituted-4-cyanotetrahydropyran compound used in the above reaction of the second invention is represented by the above formula (4).
  • R 1 has the same meaning as described above.
  • the reaction reagent used in the reaction of the second invention is represented by the above formula (5).
  • That X in the formula (5) is a leaving group, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a methanesulfonyloxy group, an ethanesulfonyloxy group and a trifluoromethane Alkylsulfonyloxy group such as sulfonyloxy group; alkoxysulfonyloxy group such as methoxysnorreonyoxy group; benzenesulfonyloxy group, p-toluenesulfonyloxy group, p-fluorobenzenesulfonyloxy group, p_ And arylsulfonyloxy groups such as bromobenzenesulfonyloxy group and p-methoxybenzene
  • the amount of the reaction reagent to be used is preferably 1.0 to 10 mol, more preferably 1.05 mol, per 1 mol of the 4-unsubstituted-4-cyanotetrahydropyran compound.
  • the base used in the reaction of the second invention includes, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogencarbonate; Alkali metal bicarbonates such as potassium bicarbonate; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal hydrides such as sodium hydride and potassium hydride; alkaline earth metal hydrides such as calcium hydride Alkali metal alkyls such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; alkali metal amines such as lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium amide, and sodium bis (trimethylsilyl) amide used. In addition, you may use these bases individually or in mixture of 2 or more types.
  • the amount of the base to be used is preferably 1.0 to 10 mol, more preferably 1.0 to 5 mol, per 1 mol of the 4-unsubstituted-4-cyanotetrahydropyran compound.
  • the reaction of the second invention is desirably performed in the presence of a solvent.
  • the solvent used is not particularly limited as long as it does not inhibit the reaction, and examples thereof include alcohols such as methanol, ethanol, isopropyl alcohol, and t_butyl alcohol; ketones such as acetone, methylethyl ketone, and methyl isobutyl ketone; Amides such as ⁇ , ⁇ -dimethylformamide, ⁇ , ⁇ _dimethylenolacetoamide, and ⁇ -methylpyrrolidone; urines such as ⁇ , ⁇ , -dimethylimidazolidinone; sulfoxides such as dimethyl sulfoxide; getyl ether; Ethers such as isopropynole ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene and xylene, but preferably amides, ethers and aromatics Hydrocarbons
  • the amount of the solvent to be used is appropriately adjusted depending on the uniformity of the reaction and the stirring property, but it is preferably 1 to 50 ml, and more preferably 2 to 4 unsubstituted-4-cyanotetrahydropyran compound lg. One is 10ml.
  • reaction of the second invention for example, after mixing and stirring a 4_unsubstituted-4-cyanotetrahydropyran compound, a base and a solvent, the reaction reagent is added, and the mixture is stirred. It is performed by a method such as reaction.
  • the reaction temperature at that time is preferably -20 180 ° C, more preferably -5 120 ° C, and the reaction pressure is not particularly limited.
  • the reaction of the second invention yields a 4-substituted-4-cyanotetrahydropyran compound, which is neutralized, extracted, filtered, concentrated, distilled, recrystallized, crystallized after completion of the reaction. It is isolated and purified by a common method such as column chromatography.
  • X is a leaving group, specifically, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom; a methanesulfonyloxy group, an ethanesulfonyloxy group, Alkyl sulfonyl / reoxy groups such as trifluoromethanesulfonyloxy group; benzenesulfonyloxy group, p-toluenesulfonyloxy group, p-bromobenzenesulfonyloxy group, p-methoxybenzenesulfonyloxy group, etc. And a reelsulfonyloxy group.
  • R 1 has the same meaning as described above.
  • Examples of the cyanating agent used in the reaction of the third invention include lithium cyanide. , Sodium cyanide, potassium cyanide, copper cyanide, iron cyanide, tetraethylammonium cyanide and the like. These cyanating agents may be used alone or in combination of two or more.
  • the amount of the cyanating agent to be used is preferably 1.010 mol, more preferably 1.1 to 5.0 mol, per 1 mol of the 4-substituted tetrahydropyran compound.
  • the reaction of the third invention is desirably performed in a solvent.
  • the solvent used is one that does not inhibit the reaction, and is not particularly limited as long as it is, for example, water; methanol, ethanol, isopropylinorenocone, t-butinoleanorecone, ethylene glycolone, Alcohols such as triethylene glycolonole; amides such as ⁇ , ⁇ -dimethylformamide, ⁇ , ⁇ _dimethylacetoamide, ⁇ -methinolepyrrolidone; ureas such as ⁇ , ⁇ '-dimethylimidazolidinone; dimethyl sulfoxide Sulfoxides, etc .; ethers, such as getyl ether, diisopropyl ether, tetrahydrofuran, dioxane; aromatic hydrocarbons, such as benzene, toluene, xylene; nitriles, such as acetonitrile
  • the amount of the solvent to be used is appropriately adjusted depending on the uniformity and stirring property of the reaction solution.
  • One 20g of the solvent to be used is appropriately adjusted depending on the uniformity and stirring property of the reaction solution.
  • the reaction of the third invention is carried out, for example, by a method of mixing a 4-substituted tetrahydropyranich compound, a cyanating agent and a solvent, and reacting the mixture with stirring.
  • the reaction temperature at that time is preferably 20 to 200 ° C, more preferably 40 to 120 ° C, and the reaction pressure is not particularly limited. Since toxic hydrogen cyanide may be generated during the reaction of the present invention, it is desirable that a base (for example, an organic amine or an alkali metal salt) is present in the system in advance.
  • quaternary ammonium salt such as tetramethylammonium chloride and tetraethylammonium bromide
  • an alkali metal halide such as sodium iodide and potassium iodide
  • the 4-unsubstituted-4-cyanotetrahydropyrani conjugate obtained by the reaction of the third invention is for example, it is isolated and purified by general methods such as neutralization, extraction, filtration, concentration, distillation, recrystallization, crystallization, and column chromatography.
  • reaction yield 0.50 g of 4-cyanotetrahydropyran was produced (reaction yield: 44%).
  • reaction solution was cooled to room temperature, and while stirring, 500 ml of water, 650 ml (7.80 mol) of concentrated hydrochloric acid and 500 ml of toluene were sequentially added.
  • the aqueous layer and the organic layer (toluene layer) were separated, and the aqueous layer was extracted three times with 500 ml of toluene.
  • the organic layer and the toluene extract were combined and concentrated under reduced pressure.
  • the obtained concentrate was distilled under reduced pressure (100 to 120 ° C, 2.0 to 2.7 kPa) to obtain 133.5 g of 4-cyanotetrahydropyran having a purity of 99% (area percentage by gas chromatography) as a colorless liquid. (Isolation yield: 93%).
  • Example 5 Under a nitrogen atmosphere, a 99% pure 4-cyanotetrahydropyran synthesized in Example 5 was placed in a 300-ml glass flask equipped with a stirrer, a thermometer, and a reflux condenser.
  • the obtained concentrated solution was distilled under reduced pressure (75-76 ° C, 1.2-1.3 kPa) to obtain 18.3 g of methyl tetrahydropyran-4-carboxylate having a purity of 98.7% (area percentage by gas chromatography) as a colorless liquid. Obtained (isolation yield: 63.5%).
  • 4-substituted or unsubstituted 4-cyanotetrahydropyran compounds can be obtained in high yield from 4-substituted or unsubstituted 4-cyanotetrahydropyran compounds under mild conditions without requiring complicated operations.
  • 4-substituted or unsubstituted tetrahydropyran-4-carboxylic acid compound or an ester thereof capable of producing a 4-carboxylic acid compound or an esterified compound thereof.
  • the present invention can provide a method for producing a compound.
  • the 4-substituted or unsubstituted tetrahydropyran-4-carboxylic acid compound or its esterified compound is a compound useful as a raw material for a pharmaceutical or an agricultural chemical or a synthetic intermediate.
  • the present invention also relates to a method for producing a 4-substituted-4-cyanotetrahydropyrani conjugate from a 4_unsubstituted-4-cyanotetrahydropyrani conjugate.
  • the 4-substituted or unsubstituted 4-cyanotetrahydropyran compound is a compound useful as a raw material of a pharmaceutical or an agricultural chemical or a synthetic intermediate.
  • the present invention further relates to a process for producing a 4-pyranated 4-substituted-4-cyanotetrahydropyran compound from a 4-substituted tetrahydropyran compound.
  • the 4-unsubstituted-4-cyanotetrahydropyrani conjugate is a compound useful as a raw material for pharmaceuticals and agricultural chemicals and as a synthetic intermediate.

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  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé pour produire un composé d'acide 4-(non)substitué tétrahydropyran-4-carboxylique ou un composé ester de celui-ci de formule (1). Dans cette formule, R1 désigne hydrogène ou un groupe hydrocarbure; R2 désigne hydrogène ou un groupe hydrocarbure éventuellement substitué; et R3 désigne hydrogène ou un groupe hydrocarbure. Le procédé de l'invention est caractérisé par la réaction d'un composé 4-(non)substitué-4-cyanotétrahydropyrane de formule (2), dans cette formule R1 et R2 sont comme définis ci-dessus, avec de l'eau ou avec un alcool de formule (3), R3 étant défini comme ci-dessus, en présence d'un acide ou d'une base.
PCT/JP2004/018942 2003-12-19 2004-12-17 Procede pour produire un compose d'acide 4-(non)substitue tetrahydropyran-4-carboxylique ou un compose ester de celui-ci Ceased WO2005058860A1 (fr)

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JP2004-174681 2004-06-11
JP2004-174680 2004-06-11
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JP2004-221524 2004-07-29
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Cited By (6)

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JP2007230942A (ja) * 2006-03-02 2007-09-13 Ube Ind Ltd ４−置換テトラヒドロピランの製造方法
WO2011012661A1 (fr) 2009-07-30 2011-02-03 Novartis Ag Dérivés de la pyridine et de la pyrazine en tant que modulateurs de la protéine kinase
JP2012082211A (ja) * 2011-12-09 2012-04-26 Ube Industries Ltd ４−置換テトラヒドロピランの製造方法
WO2012101062A1 (fr) 2011-01-28 2012-08-02 Novartis Ag Composés bi-hétéroaryles substitués en tant qu'inhibiteurs de cdk9 et leurs utilisations
WO2012101065A2 (fr) 2011-01-28 2012-08-02 Novartis Ag Composés de pyrimidine biarylamine et leurs utilisations
JP2013189445A (ja) * 2003-12-19 2013-09-26 Ube Industries Ltd ４−置換又は非置換テトラヒドロピラン−４−カルボン酸化合物又はそのエステル化合物の製法

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JP2013189445A (ja) * 2003-12-19 2013-09-26 Ube Industries Ltd ４−置換又は非置換テトラヒドロピラン−４−カルボン酸化合物又はそのエステル化合物の製法
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WO2011012661A1 (fr) 2009-07-30 2011-02-03 Novartis Ag Dérivés de la pyridine et de la pyrazine en tant que modulateurs de la protéine kinase
WO2012101062A1 (fr) 2011-01-28 2012-08-02 Novartis Ag Composés bi-hétéroaryles substitués en tant qu'inhibiteurs de cdk9 et leurs utilisations
WO2012101065A2 (fr) 2011-01-28 2012-08-02 Novartis Ag Composés de pyrimidine biarylamine et leurs utilisations
JP2012082211A (ja) * 2011-12-09 2012-04-26 Ube Industries Ltd ４−置換テトラヒドロピランの製造方法

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