EP1448788A4 - Syntheseverfahren für (r)-1-(3,5-bis(trifluormethyl)-phenyl)ethan-1-ol und dessen ester mit dynamisch-kinetischer auflösung - Google Patents

Syntheseverfahren für (r)-1-(3,5-bis(trifluormethyl)-phenyl)ethan-1-ol und dessen ester mit dynamisch-kinetischer auflösung

Info

Publication number
EP1448788A4
EP1448788A4 EP02791261A EP02791261A EP1448788A4 EP 1448788 A4 EP1448788 A4 EP 1448788A4 EP 02791261 A EP02791261 A EP 02791261A EP 02791261 A EP02791261 A EP 02791261A EP 1448788 A4 EP1448788 A4 EP 1448788A4
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
compound
aryl
bis
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.)
Withdrawn
Application number
EP02791261A
Other languages
English (en)
French (fr)
Other versions
EP1448788A2 (de
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
Publication of EP1448788A2 publication Critical patent/EP1448788A2/de
Publication of EP1448788A4 publication Critical patent/EP1448788A4/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • 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)
EP02791261A 2001-11-19 2002-11-15 Syntheseverfahren für (r)-1-(3,5-bis(trifluormethyl)-phenyl)ethan-1-ol und dessen ester mit dynamisch-kinetischer auflösung Withdrawn EP1448788A4 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US33303901P 2001-11-19 2001-11-19
US333039P 2001-11-19
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

Publications (2)

Publication Number Publication Date
EP1448788A2 EP1448788A2 (de) 2004-08-25
EP1448788A4 true EP1448788A4 (de) 2006-03-29

Family

ID=23300996

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02791261A Withdrawn EP1448788A4 (de) 2001-11-19 2002-11-15 Syntheseverfahren für (r)-1-(3,5-bis(trifluormethyl)-phenyl)ethan-1-ol und dessen ester mit dynamisch-kinetischer auflösung

Country Status (3)

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

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 (en) * 2003-04-23 2004-11-04 Miteni S.P.A. Process for the manufacture of 3,5-bis(trifluoromethyl)phenyl-1-hydroxyethane and derivative thereof
US20050171393A1 (en) 2003-07-15 2005-08-04 Lorkovic Ivan M. Hydrocarbon synthesis
CA2532367C (en) 2003-07-15 2013-04-23 Grt, Inc. Hydrocarbon synthesis
AT500556A1 (de) * 2004-03-18 2006-01-15 Dsm Fine Chem Austria Gmbh Verfahren zur herstellung von chiralen, sekundären alkoholen
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes 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
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
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
EP1710221A1 (de) * 2005-04-07 2006-10-11 DSM IP Assets B.V. Verfahren zur Herstellung eines optisch-aktiven Esters
EP2457887A1 (de) 2006-02-03 2012-05-30 GRT, Inc. Kontinuierliches Verfahren zur Umwandlung von Erdgas in flüssige Kohlenwasserstoffe
BRPI0707490A2 (pt) 2006-02-03 2011-05-03 Grt Inc separação de gases leves de halogênios
KR20100027141A (ko) 2007-05-24 2010-03-10 지알티, 인코포레이티드 가역적으로 할로겐화수소를 흡수 및 방출할 수 있는 존 반응기
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
AU2009270801B2 (en) 2008-07-18 2014-04-24 Reaction 35, Llc 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 (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963492A (en) * 1987-12-23 1990-10-16 Hoechst Aktiengesellschaft Method for the enzymatic racemate resolution of racemic alcohols with/in vinyl esters by transesterification

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003503468A (ja) * 1999-07-01 2003-01-28 メルク エンド カムパニー インコーポレーテッド 水素移動型不斉還元による（ｒ）−１−（３，５−ビス（トリフルオロメチル）フェニル）エタン−１−オールの合成方法
NL1015313C2 (nl) * 2000-05-26 2001-11-27 Dsm Nv Werkwijze voor de bereiding van enantiomeer verrijkte esters en alcoholen.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963492A (en) * 1987-12-23 1990-10-16 Hoechst Aktiengesellschaft Method for the enzymatic racemate resolution of racemic alcohols with/in vinyl esters by transesterification

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ALLEN, ANNETTE D. ET AL: "Solvolysis of 1-arylethyl tosylates. Kinetic and stereochemical tests for solvent participation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 107(15), 4513-19 CODEN: JACSAT; ISSN: 0002-7863, 1985, XP002364112 *
DINH, PHI M. ET AL: "Catalytic racemization of alcohols: applications to enzymic resolution reactions", TETRAHEDRON LETTERS , 37(42), 7623-7626 CODEN: TELEAY; ISSN: 0040-4039, 1996, XP004068864 *
KRAEMER, ROLAND ET AL: "Chirale Halbsandwich - Komplexe von Cobalt(III), Rhodium(III), Iridium(III), und Ruthenium(II) mit alpha.-Aminosäureamid-, Glycinnitril- und Peptidester-Liganden", CHEMISCHE BERICHTE , 126(9), 1969-80 CODEN: CHBEAM; ISSN: 0009-2940, 1993, XP002090293 *
LARSSON, ANNA L. E. ET AL: "Enzymic resolution of alcohols coupled with ruthenium-catalyzed racemization of the substrate alcohol", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION IN ENGLISH , 36(11), 1211-1212 CODEN: ACIEAY; ISSN: 0570-0833, 1997, XP002176122 *

Also Published As

Publication number Publication date
WO2003043575A3 (en) 2003-10-16
WO2003043575A2 (en) 2003-05-30
AU2002365968A1 (en) 2003-06-10
EP1448788A2 (de) 2004-08-25

Similar Documents

Publication Publication Date Title
WO2003043575A2 (en) Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution
US6841691B2 (en) Process for the preparation of enantiomerically enriched esters and alcohols
Szöri et al. Heterogeneous asymmetric reactions: Part 28. Efficient and practical method for the preparation of (R)-and (S)-α-hydroxy esters by the enantioselective heterogeneous catalytic hydrogenation of α-ketoesters
EP2203562B1 (de) Verfahren zur herstellung eines enantiomerisch und/oder diastereomerisch angereicherten esters, thioesters, alkohols oder thiols
AU2001278640B2 (en) Process for preparing (-)menthol and similar compounds
FR2724184A1 (fr) Procede de resolution d'un melange d'alcools stereoisomeres
US4921798A (en) Synthesis of (aryl or arylalkyl)-3-hydroxy propionic acids and aryl alkanediols having high optical purity
Wallner et al. Chemo-enzymatic enantio-convergent asymmetric total synthesis of (S)-(+)-dictyoprolene using a kinetic resolution—stereoinversion protocol
AU2001278640A1 (en) Process for preparing (-)menthol and similar compounds
Cipiciani et al. Primary allenic alcohols of high optical purity via lipase catalyzed resolution
Itoh et al. Synthesis of optically active gem-difluorocyclopropanes through a chemo-enzymatic reaction strategy
WO2005014509A1 (en) Process for the preparation of enantiomerically enriched esters and alcohols
JP3704731B2 (ja) 光学活性３−ヒドロキシヘキサン酸類の製造方法
JP2542872B2 (ja) 光学活性な不飽和アルコ―ル及びそのエステル体の製造法
JP3049403B2 (ja) 光学活性トランス−２−アリール−１−シクロヘキサノール誘導体およびその製造法
Ranchoux et al. Enzymatic desymmetrization of prochiral 2, 3-bis (acetoxymethyl) bicyclo [2.2. 1] hepta-2, 5-diene and 2, 3-bis (hydroxymethyl) bicyclo [2.2. 1] hepta-2, 5-diene
Hazelard et al. The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: Preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode
JP2896583B2 (ja) 光学活性なジシクロペンタジエン類
Banerji et al. Enzymes as a tool for optical resolution of (±) α-methyl-4-(2-methylpropyl) benzeneacetic acid (ibuprofen)
WO2005095629A1 (en) Process for the preparation of enantiomerically enriched esters and alcohols by means of azeotropically dried enzyme compositions
KR100559259B1 (ko) 동적속도론적 광학 분할에 의한 (ｓ)-2-아릴프로피온산유도체의 제조방법
JP2011042661A (ja) 光学活性な含フッ素アルコール類の製造方法及び光学活性な含フッ素２−ヒドロキシアルカンアミド又は／及び光学活性な含フッ素アルコールの製造方法、並びに光学活性な含フッ素乳酸又はその誘導体の製造方法
EP1985603A1 (de) Verfahren zur Herstellung von Difluorcyclohexansäurederivaten
JPH10248593A (ja) ω−アルコキシ−１，１，１−トリフルオロ−２−アルカノールの光学分割方法
Jennings Application of enzyme-mediated esterifications to the resolution of chiral alcohols and phosphines

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20040621

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

A4 Supplementary search report drawn up and despatched

Effective date: 20060210

17Q First examination report despatched

Effective date: 20061222

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20070503