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WO2005026190A1 - Procede de production d'amine cyclique - Google Patents

Procede de production d'amine cyclique Download PDF

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Publication number
WO2005026190A1
WO2005026190A1 PCT/JP2004/013029 JP2004013029W WO2005026190A1 WO 2005026190 A1 WO2005026190 A1 WO 2005026190A1 JP 2004013029 W JP2004013029 W JP 2004013029W WO 2005026190 A1 WO2005026190 A1 WO 2005026190A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon
ketone
amino
palladium
rhodium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2004/013029
Other languages
English (en)
Japanese (ja)
Inventor
Satoru Yada
Yuzuru Takagi
Masahiro Tsukui
Tomoaki Ikenaga
Kumiko Matsushita
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nihon University
Original Assignee
Nihon University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nihon University filed Critical Nihon University
Priority to JP2005513868A priority Critical patent/JPWO2005026190A1/ja
Publication of WO2005026190A1 publication Critical patent/WO2005026190A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/828—Platinum

Definitions

  • the present invention relates to the removal of aminated cyclized ⁇ from $ 3 ⁇ 4 ⁇ .
  • Aminosteroid is known to have effects such as an antisensitivity effect and an anticancer effect.
  • 17-aminosteroids are anti-cancer drugs described in [
  • Non-Patent Document 1 the oxime form of estrone is reduced with sodium to obtain 17 j3-amino-1, 3, 5 (10) — Estratrien 3—;
  • Non-patent document 1 Christina Lemini, Elia Cruz-Ramos et al., A comparative structural study of the steroid e imers: 17 j3 -amino-1, 3, 5 (10) _estratrien_3_ol, ⁇
  • estrone was used as the raw material:
  • the present invention is to solve such a conventional problem.
  • An object of the present invention is to provide a method for producing an aminoi-like compound such as a steroid by a simple and high yield.
  • the present invention provides a process for producing an aminated cyclic compound in which a cyclic ketone in which at least one carbon atom at the ⁇ - position of the carbonyl group is a tertiary or quaternary is reacted with 7_k element and ammonia.
  • the amylation was carried out in the presence of an amyloid in the presence of an ammodime salt with a white turtle or a salt thereof containing %% of the thiocyanate.
  • the term "white scythe” refers to ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium among the elements belonging to Groups 8 to 10 of the periodic table. (Ir) and platinum (Pt). Further, as examples of the conversion of a white man, there may be mentioned, for example, the elimination of the platinum group, halogen compounds such as bromine fiber and quince, « ⁇ , ⁇ » ⁇ , and rooster ⁇ .
  • Displeased ⁇ S corner butterfly is a carrier of carbon, silica, alumina, silica-aluminum, especially a corner butterfly supported on carbon, if f is white. Good. As a result, the conversion of the starting material can be improved, and the yield of the finally obtained amino conjugate can be improved.
  • the disgusting male horn butterfly is made of nondium, rhodium, rhodium, ruthenium-carbon (Ru-C), rhodium-carbon (Rh-C), or palladium-carbon (Pd-C). Either force is preferred, and more preferably rhodium, palladium, rhodium-carbon, or palladium-mukabon! It is preferable that it is a paradigm or paraffin foam.
  • the production process of the present invention is suitably used for producing an aminosteroid by amination of a steroid ketone, and particularly, a steroid ketone in which the C-17 position is a carbonyl group (ketone group). It is preferably used, for example, in estrone's Amino-dani.
  • the annihilation angle ⁇ is a moth in which a sickle or its conversion ⁇ 5% is supported on a charcoal carrier ⁇ 1 0 0 wt 0/0 or more with respect to, preferably 1 0 0-4 0 0 wt%, more preferably 3 0 0-4 0 that Do 0 wt%.
  • ⁇ amount of ⁇ Anmoniumu salt is preferably 3 0 wt 0/0 or more with respect to tfjf ⁇ ketone.
  • [0017] is, for example, from 30 to 00 ° C, preferably from 50 to 70 ° C, particularly preferably from 60 to 70 ° C.
  • a cyclic ketone such as a steroid ketone (a carbonyl group) is reduced with hydrogen and ammonia using an angle ⁇ to form an ammonium salt.
  • the present invention provides tSt removal of aminated cyclization using an adhesive layer to suppress the hydroxylation of the ketone and to improve the yield of the amino compound.
  • an amino acid compound such as amino steroid can be produced easily and in good yield with good yield.
  • the carbonyl group of the cyclic ketone is converted to tf ⁇ S angle, including white ⁇ ⁇ or its conversion, and ammonia.
  • tf ⁇ S angle including white ⁇ ⁇ or its conversion, and ammonia.
  • 7_K element and ⁇ ⁇ ⁇ amino by amination with ammonia! ⁇ To obtain a compound.
  • the cyclic ketone used in the present invention includes, for example, a cyclic ketone in which at least one hydrogen at the carbonyl group is woven, ie, a carbon ( ⁇ -carbon) force of at least one of the carbonyl groups. He is a quaternary carbon cyclic ketone. More specifically, an alicyclic ketone (steroid ketone) having a steroid skeleton in which at least one hydrogen at the tertiary position of the carbyl group has been added is exemplified.
  • the steroid skeleton refers to a pentaphenanthrene skeleton having a peroxy mouth.
  • examples of 3 ⁇ 4 which substitute for the hydrogen at the ⁇ -position include, but are not particularly limited to, an alkyl group (eg, methyl group) force S.
  • the rings A to D in the steroid skeleton may have an edible bond.
  • the manufacturing method of the present invention is particularly used for a steroid ketone or a tool having a carbonyl group (ketone group) at the C-17 position, such as estrone represented by the following formula (I).
  • ⁇ S angle butterfly containing ⁇ S of white sickle or ⁇ S of ⁇
  • white male refers to the elements belonging to groups 8 to 10 of the periodic table: nonium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), And platinum (Pt).
  • examples of the miscellaneous ⁇ M compounds include: « ⁇ , bromine ugly, halogenated ⁇ !, « ⁇ , « ⁇ , and the like.
  • the white base or its compound 1 may be converted to a carrier such as carbon, silicon, anoremina, or silica-alumina, preferably carbon. This is preferable since the transfer of the separated substance is improved. Also such gold
  • the cut ratio of the J3 body is high, that is, the yield of] 3 body is high, ruthenium, rhodium, palladium, and white palladium-carbon are preferable, and palladium is more preferable. White and palladium-carbon are preferable, and platinum is particularly preferable.
  • the content of the or SS compound in the angle 0 is desirably 0:! To 10%.
  • 5% ruthenium-carbon 5% 111-, 5% rhodium-carbon (5% Rh-C), and 5% palladium-carbon (5% Pd-C) are preferable.
  • the amount of mouth of male angle ⁇ is a cyclic ketone (eg: against steroid ketone), 1 0 0 wt 0/0 or more, preferably 1 0 0-4 0 0 wt 0 do more preferably is 3 0 0-4 0 0 wt%.
  • the pot size of the pot corner butterfly is less than the value shown below, there is a tendency for body S to be delayed.
  • the effect of the square fiber does not change. Therefore, it is desirable to be within the above-mentioned fiber because of the cost.
  • ammonium salt used in the present invention includes, for example, ammonium fluoride, ammonium chloride, ammonium bromide, ammonium iodide, cock ammonium, and ammonium ammonium. Of these, halogenated ammonium is preferred, and ammonium chloride is particularly preferred.
  • the excitation ft of the ammonia is 30fi *% RJi with respect to the ketone serving.
  • ammonia is used for the amino acid core, and the amount of ammonia is 1 mol or more, preferably 10 mol, per 1 mol of the raw material cyclic ketone (eg, steroid ketone). More preferably, it is preferably at least 50 mol.
  • the temperature is preferably 30 to 100 ° C, more preferably 50 to 70 ° C,
  • the 7_R elemental pressure is preferably 2 to 8 MPa, particularly preferably 4 to 6 MPa. If the reaction pressure is in the range above 3 ⁇ 4g, ⁇ iHjS does not occur and (Steroid amine) yield tends to increase.
  • the fierce material used in the present invention is not particularly limited, but is preferably a nada which well dissolves ammonia, a cyclic ketone, and an ammonium salt.
  • a polar wister such as methanol, ethanol, or isopropyl alcohol may be used.
  • the amount of Nada is not particularly limited, it is usually 1 to 100 times, preferably 10 to 500 times the amount of the cyclic ketone.
  • the addition amount of ammonium salt is not particularly limited, and a system containing a cyclic ketone may be advocated almost simultaneously with a horned butterfly. In addition, it is possible to excite the ammonium salt before adding the horn butterfly, and then add ⁇ .
  • the addition of an ammonium salt suppresses the alcoholization of the secondary ketone and promotes the amination of the ketone ⁇ S ⁇ . It is thought that the yield of sulfide is improved.
  • Another H of the present invention is a cyclic ketone such as a steroid ketone, which is reductively oxidized with elemental and ammonia by using Tsutomu Kakuto; finally, an ammonium salt is formed.
  • a cyclic ketone such as a steroid ketone, which is reductively oxidized with elemental and ammonia by using Tsutomu Kakuto; finally, an ammonium salt is formed.
  • the aminated cyclization ⁇ ⁇ ⁇ which suppresses the hydroxylation of the ketone which is an auxiliary ⁇ ⁇ and improves the yield of the aminated cyclization ⁇
  • Note that the above description may be appropriately taken into account in addition to ** regarding the tut of Toshiya.
  • the obtained product was measured by gas chromatography (hereinafter, also referred to as GC).
  • Example 1 was carried out in the same manner as in Example 1 except that instead of luteuium, 0.20 g of a 5% ruthenium-carbon supported catalyst was used. The results are shown in Table 1.
  • Example 1 was carried out in the same manner as in Example 1 except that the metal catalyst shown in Table 1 was used instead of ruthenium. The results are shown in Table 1.
  • Example 2 the metal catalyst of Table 1 was used instead of the 5% ruthenium-carbon supported catalyst. Except having used, it carried out similarly to Example 2. Table 1 shows the results.
  • Example 1 was carried out in the same manner as in Example 1 except that the metal catalyst shown in Table 1 was used instead of ruthenium, and a salty ammonium was used. The results are shown in Table 1.
  • the ratio of the body to the body is the value obtained from the measurement results of 'HNM R and GC (trade name: CBP-1 (50 m), non-polar, manufactured by Shimadzu Corporation, Column). Those not listed are not measured.
  • Example 2 The reaction was carried out in the same manner as in Example 1 except that the conditions shown in Table 2 were used and the measurement was performed using GC (Column: Agilent Technologies, Inc., trade name: DB-1701 (60 m), polarity). The result See Table 2.
  • Conversion indicates the rate at which the starting material was converted.
  • the conversion data shown in the table are based on the data of GC (column Agilent Technologies, trade name: DB-170] (60 m), polarity).
  • ⁇ improves the conversion of the starting material and improves the yield of steroidamine (III), compared with ⁇ using the simple substance as square fiber. There is a tendency.
  • the harm ij between the ⁇ -isomer of the target substance steroidamine (III) and the body is determined by a palladium-based fiber (Pd, Pd-C) and a white recording angle (Pt).
  • ⁇ especially 3 bodies ⁇ J3 ⁇ 43 ⁇ 4 7 this.
  • amination cyclization such as amino steroid can be easily performed

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Steroid Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Procédé permettant de produire de l'amine cyclique facilement et avec un haut rendement. Ce procédé de production d'amine cyclique consiste à aminer, avec de l'hydrogène et de l'ammoniac, une cétone cyclique dans laquelle au moins l'un des atomes de carbone dans les positions α par rapport au groupe carbonyle est tertiaire ou quaternaire, l'amination étant effectuée en présence à la fois d'un catalyseur métallique contenant un métal du groupe platine ou un composé de ce métal et un sel d'ammonium. Le catalyseur métallique est de préférence choisi parmi ruthénium, rhodium, palladium, ruthénium-carbone, rhodium-carbone et palladium-carbone.
PCT/JP2004/013029 2003-09-10 2004-09-08 Procede de production d'amine cyclique Ceased WO2005026190A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005513868A JPWO2005026190A1 (ja) 2003-09-10 2004-09-08 アミノ化環状化合物の製造方法

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JP2003-318271 2003-09-10
JP2003318271 2003-09-10

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WO2005026190A1 true WO2005026190A1 (fr) 2005-03-24

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5212109B2 (ja) * 2006-11-10 2013-06-19 和光純薬工業株式会社 金属触媒担持炭素−エチレンジアミン複合体及びその製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56120699A (en) * 1980-01-30 1981-09-22 Akzo Nv 177aminoo166hydroxysteroid of novel androstane and estrane* its derivative and its drug composition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56120699A (en) * 1980-01-30 1981-09-22 Akzo Nv 177aminoo166hydroxysteroid of novel androstane and estrane* its derivative and its drug composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LEMINI C. ET AL.: "A comparative structural study of the steroid epimers: 17beta-amino-1,3,5(10)-estratrien-3-ol, 17alpha-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by HNMR, and x-ray differentiation analysis", STEROIDS, vol. 63, no. 11, 1988, pages 556 - 564, XP004144116 *
SHINOZAWA J. ET AL.: "Hakkinozoku kinzoku shokubai ni yoru 5alpha-cholestane-3-on no sentakuteki kangen amino-Ka hanno", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 81 SHUNKI NENKAI 2002 NEN KOEN YOKOSHU I, 2002, pages 576, XP002985739 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5212109B2 (ja) * 2006-11-10 2013-06-19 和光純薬工業株式会社 金属触媒担持炭素−エチレンジアミン複合体及びその製造方法

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