WO2003043575A3 - Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution - Google Patents

Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution 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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Prior art keywords
ethan
trifluoromethyl
bis
esters
phenyl
Prior art date
Application number
PCT/US2002/036969
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French (fr)
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WO2003043575A2 (en
Inventor
Quirinus Bernardus Broxterman
Gerardus Karel Maria Verzijl
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Merck & Co Inc
Quirinus Bernardus Broxterman
Gerardus Karel Maria Verzijl
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Publication date
Application filed by Merck & Co Inc, Quirinus Bernardus Broxterman, Gerardus Karel Maria Verzijl filed Critical Merck & Co Inc
Priority to AU2002365968A priority Critical patent/AU2002365968A1/en
Priority to EP02791261A priority patent/EP1448788A4/en
Publication of WO2003043575A2 publication Critical patent/WO2003043575A2/en
Publication of WO2003043575A3 publication Critical patent/WO2003043575A3/en

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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)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (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

The present invention is concerned with novel processes for the preparation of (R)-1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol and esters thereof via dynamic kinetic resolution. These compounds are useful as intermediates in the synthesis of compounds which possess pharmacological activity.
PCT/US2002/036969 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 WO2003043575A2 (en)

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 (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

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 (en) 2003-05-30
WO2003043575A3 true WO2003043575A3 (en) 2003-10-16

Family

ID=23300996

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/036969 WO2003043575A2 (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

Country Status (3)

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

Families Citing this family (22)

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US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
AU2003230221A1 (en) * 2003-04-23 2004-11-19 Miteni S.P.A. Process for the manufacture of 3,5-bis(trifluoromethyl)phenyl-1-hydroxyethane and derivative thereof
CA2532367C (en) 2003-07-15 2013-04-23 Grt, Inc. Hydrocarbon synthesis
US20050171393A1 (en) 2003-07-15 2005-08-04 Lorkovic Ivan M. Hydrocarbon synthesis
AT500556A1 (en) * 2004-03-18 2006-01-15 Dsm Fine Chem Austria Gmbh METHOD FOR THE PRODUCTION OF CHIRAL, SECONDARY ALCOHOLS
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8173851B2 (en) 2004-04-16 2012-05-08 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
US20080275284A1 (en) 2004-04-16 2008-11-06 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
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
EP1710221A1 (en) * 2005-04-07 2006-10-11 DSM IP Assets B.V. Process for the preparation of an optically active ester
EP1993951B1 (en) 2006-02-03 2014-07-30 GRT, Inc. Separation of light gases from bromine
NZ588129A (en) 2006-02-03 2012-06-29 Grt Inc Continuous process for converting natural gas to liquid hydrocarbons
JP2010528054A (en) 2007-05-24 2010-08-19 ジーアールティー インコーポレイテッド Zone reactor incorporating reversible hydrogen halide capture and release
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
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8367884B2 (en) 2010-03-02 2013-02-05 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 (en) * 2016-08-17 2018-09-21 沧州普瑞东方科技有限公司 A method of synthesis 3,5- bis trifluoromethyl acetophenones

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002326A1 (en) * 1999-07-01 2001-01-11 Merck & Co., Inc. Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol by asymmetric transfer hydrogenation
WO2001090396A1 (en) * 2000-05-26 2001-11-29 Dsm N.V. Process for the preparation of enantiomerically enriched esters and alcohols

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3743824C2 (en) * 1987-12-23 1997-03-06 Hoechst Ag Process for the enzymatic resolution of racemic alcohols with / in vinyl esters by transesterification

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002326A1 (en) * 1999-07-01 2001-01-11 Merck & Co., Inc. Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol by asymmetric transfer hydrogenation
WO2001090396A1 (en) * 2000-05-26 2001-11-29 Dsm N.V. Process for the preparation of enantiomerically enriched esters and alcohols

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

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