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WO2003043575A3 - Procede de synthese de (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol et de certains de ses esters par resolution cinetique dynamique - Google Patents

Procede de synthese de (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol et de certains de ses esters par resolution cinetique dynamique Download PDF

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Publication number
WO2003043575A3
WO2003043575A3 PCT/US2002/036969 US0236969W WO03043575A3 WO 2003043575 A3 WO2003043575 A3 WO 2003043575A3 US 0236969 W US0236969 W US 0236969W WO 03043575 A3 WO03043575 A3 WO 03043575A3
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WO
WIPO (PCT)
Prior art keywords
ethan
trifluoromethyl
bis
esters
phenyl
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/US2002/036969
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English (en)
Other versions
WO2003043575A2 (fr
Inventor
Quirinus Bernardus Broxterman
Gerardus Karel Maria Verzijl
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Priority to AU2002365968A priority Critical patent/AU2002365968A1/en
Priority to EP02791261A priority patent/EP1448788A4/fr
Publication of WO2003043575A2 publication Critical patent/WO2003043575A2/fr
Publication of WO2003043575A3 publication Critical patent/WO2003043575A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
    • C07C29/92—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound by a consecutive conversion and reconstruction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux procédés de préparation de (R)-1-(3,5-bis(trifluorométhyl)phényl)étan-1-ol et de certains de ses esters, par résolution cinétique dynamique. Ces composés peuvent servir de produits intermédiaires dans la synthèse de composés présentant une activité pharmacologique.
PCT/US2002/036969 2001-11-19 2002-11-15 Procede de synthese de (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol et de certains de ses esters par resolution cinetique dynamique Ceased WO2003043575A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002365968A AU2002365968A1 (en) 2001-11-19 2002-11-15 Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution
EP02791261A EP1448788A4 (fr) 2001-11-19 2002-11-15 Procede de synthese de (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol et de certains de ses esters par resolution cinetique dynamique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33303901P 2001-11-19 2001-11-19
US60/333,039 2001-11-19

Publications (2)

Publication Number Publication Date
WO2003043575A2 WO2003043575A2 (fr) 2003-05-30
WO2003043575A3 true WO2003043575A3 (fr) 2003-10-16

Family

ID=23300996

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/036969 Ceased WO2003043575A2 (fr) 2001-11-19 2002-11-15 Procede de synthese de (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol et de certains de ses esters par resolution cinetique dynamique

Country Status (3)

Country Link
EP (1) EP1448788A4 (fr)
AU (1) AU2002365968A1 (fr)
WO (1) WO2003043575A2 (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
WO2004094353A1 (fr) * 2003-04-23 2004-11-04 Miteni S.P.A. Procede de fabrication de 3,5-bis(trifluoromethyl)phenyl-1-hydroxyethane et derive dudit compose
CA2532367C (fr) 2003-07-15 2013-04-23 Grt, Inc. Synthese d'hydrocarbures
US20050171393A1 (en) 2003-07-15 2005-08-04 Lorkovic Ivan M. Hydrocarbon synthesis
AT500556A1 (de) * 2004-03-18 2006-01-15 Dsm Fine Chem Austria Gmbh Verfahren zur herstellung von chiralen, sekundären alkoholen
US20080275284A1 (en) 2004-04-16 2008-11-06 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7244867B2 (en) 2004-04-16 2007-07-17 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US20060100469A1 (en) 2004-04-16 2006-05-11 Waycuilis John J Process for converting gaseous alkanes to olefins and liquid hydrocarbons
EP1710221A1 (fr) * 2005-04-07 2006-10-11 DSM IP Assets B.V. Procédé de préparation d'un ester optiquement active
BRPI0707490A2 (pt) 2006-02-03 2011-05-03 Grt Inc separação de gases leves de halogênios
MX2008009911A (es) 2006-02-03 2009-02-27 Grt Inc Proceso continuo para convertir gas natural a hidrocarburos liquidos.
CA2687589A1 (fr) 2007-05-24 2008-12-04 Grt, Inc. Reacteur a zones comprenant la capture et la liberation reversibles d'halogenure d'hydrogene
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
NZ591207A (en) 2008-07-18 2013-03-28 Grt Inc Continuous process for converting natural gas to liquid hydrocarbons
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
CN106278846B (zh) * 2016-08-17 2018-09-21 沧州普瑞东方科技有限公司 一种合成3,5-双三氟甲基苯乙酮的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002326A1 (fr) * 1999-07-01 2001-01-11 Merck & Co., Inc. Synthese de (r)-1-(3,5-bis(trifluoromethyle)-phenyle)ethan-1-ol par hydrogenation a transfert asymetrique
WO2001090396A1 (fr) * 2000-05-26 2001-11-29 Dsm N.V. Procede de preparation d'esters et d'alcools enrichis en enantiomeres

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3743824C2 (de) * 1987-12-23 1997-03-06 Hoechst Ag Verfahren zur enzymatischen Racematspaltung von racemischen Alkoholen mit/in Vinylestern durch Umesterung

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002326A1 (fr) * 1999-07-01 2001-01-11 Merck & Co., Inc. Synthese de (r)-1-(3,5-bis(trifluoromethyle)-phenyle)ethan-1-ol par hydrogenation a transfert asymetrique
WO2001090396A1 (fr) * 2000-05-26 2001-11-29 Dsm N.V. Procede de preparation d'esters et d'alcools enrichis en enantiomeres

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KOH ET AL.: "Enzymatic resolution of secondary alcohols coupled with ruthenium-catalyzed racemization without hydrogen mediator", TETRAHEDRON LETTERS, vol. 40, no. 34, 1999, pages 6281 - 6284, XP004174031 *
PERSSON ET AL.: "Ruthenium and enzyme-catalyzed dynamic kinetic resolution of secondary alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 8, 1999, pages 1645 - 1650, XP002158577 *
See also references of EP1448788A4 *

Also Published As

Publication number Publication date
EP1448788A4 (fr) 2006-03-29
AU2002365968A1 (en) 2003-06-10
WO2003043575A2 (fr) 2003-05-30
EP1448788A2 (fr) 2004-08-25

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