DE69505226T2 - Verfahren zur herstellung von (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentanessigsäure - Google Patents

Verfahren zur herstellung von (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentanessigsäure

Info

Publication number
DE69505226T2
DE69505226T2 DE69505226T DE69505226T DE69505226T2 DE 69505226 T2 DE69505226 T2 DE 69505226T2 DE 69505226 T DE69505226 T DE 69505226T DE 69505226 T DE69505226 T DE 69505226T DE 69505226 T2 DE69505226 T2 DE 69505226T2
Authority
DE
Germany
Prior art keywords
acid
pentyl
oxo
cis
producing
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.)
Expired - Lifetime
Application number
DE69505226T
Other languages
English (en)
Other versions
DE69505226D1 (de
Inventor
Valentin Rautenstrauch
Jean-Jacques Riedhauser
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.)
Firmenich SA
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Publication of DE69505226D1 publication Critical patent/DE69505226D1/de
Application granted granted Critical
Publication of DE69505226T2 publication Critical patent/DE69505226T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
    • B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/11—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/205—Saturated compounds having only one carboxyl group and containing keto groups containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
    • C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • 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
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/30—Non-coordinating groups comprising sulfur
    • B01J2540/32—Sulfonic acid groups or their salts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
DE69505226T 1994-06-23 1995-06-21 Verfahren zur herstellung von (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentanessigsäure Expired - Lifetime DE69505226T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH200694 1994-06-23
PCT/IB1995/000505 WO1996000206A1 (fr) 1994-06-23 1995-06-21 Procede pour la preparation de l'acide (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentaneacetique

Publications (2)

Publication Number Publication Date
DE69505226D1 DE69505226D1 (de) 1998-11-12
DE69505226T2 true DE69505226T2 (de) 1999-03-25

Family

ID=4223707

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69505226T Expired - Lifetime DE69505226T2 (de) 1994-06-23 1995-06-21 Verfahren zur herstellung von (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentanessigsäure

Country Status (5)

Country Link
US (1) US5728866A (de)
EP (1) EP0715615B1 (de)
JP (1) JP3053872B2 (de)
DE (1) DE69505226T2 (de)
WO (1) WO1996000206A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4063875B2 (ja) * 1995-11-22 2008-03-19 フイルメニツヒ ソシエテ アノニム ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用
US6214763B1 (en) 1997-05-20 2001-04-10 Firmenich Sa Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates
EP0920354B1 (de) * 1997-05-20 2003-12-03 Firmenich Sa Ruthenium-katalysatoren und ihre verwendung zur asymmetrischen hydrierung von substraten mit schwacher koordination
GB9807888D0 (en) * 1998-04-09 1998-06-10 Chirotech Technology Ltd Asymmetric hydrogenation
US8603502B2 (en) 2002-02-04 2013-12-10 L'oreal S.A. Compositions comprising jasmonic acid derivatives and use of these derivatives
FR2835525B1 (fr) 2002-02-04 2006-02-10 Oreal Nouveaux composes, compositions les comprenant et leur utilisation pour favoriser la desquamation
ITMI20031143A1 (it) * 2003-06-06 2004-12-07 Univ Pavia Processo enantioselettivo per la preparazione di
WO2005097811A1 (ja) * 2004-03-30 2005-10-20 Takasago International Corporation ホスフィン化合物、それを配位子とする遷移金属錯体及び光学活性カルボン酸の製造法
GB0409011D0 (en) * 2004-04-23 2004-05-26 Biofutures Pi Ltd Chemical compounds and use thereof in agriculture
JP4667027B2 (ja) * 2004-12-09 2011-04-06 旭化成イーマテリアルズ株式会社 シス−２、３−ジ置換シクロペンタノンの製造方法
JP5711209B2 (ja) 2010-03-04 2015-04-30 高砂香料工業株式会社 均一系不斉水素化触媒
EP3118192A4 (de) * 2014-03-14 2017-12-13 Takeda Pharmaceutical Company Limited Prozess zur herstellung einer heterocyclischen verbindung
CN112638861A (zh) * 2018-12-19 2021-04-09 弗门尼舍有限公司 制备顺式-α,β-取代的环戊酮的方法
KR200493799Y1 (ko) * 2019-01-10 2021-06-09 주식회사 리더스원홀딩스 주류 분배 장치

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH382731A (fr) * 1960-02-25 1964-10-15 Firmenich & Cie Procédé pour la préparation de céto-esters alicycliques
CH514541A (de) * 1969-03-10 1971-10-31 Givaudan & Cie Sa Verfahren zur Herstellung von (2-Pentyl-3-keto-1-cyclopent)-yl-essigsäuremethylester
NL6918228A (en) * 1969-12-04 1971-06-08 Aliphatic keto-esters used in perfumes
US3954834A (en) * 1970-11-04 1976-05-04 Polak's Frutal Works N.V. Alicyclic ketoesters and process for their manufacture
FR2119177A5 (de) * 1970-12-23 1972-08-04 Roure Bertrand Dupont Sa
US4014919A (en) * 1974-03-01 1977-03-29 The Dow Chemical Company Process for preparing methyl jasmonate and related compounds
JPS5217021B2 (de) * 1974-05-02 1977-05-12
FR2321876A1 (fr) * 1975-08-29 1977-03-25 Roussel Uclaf Nouveaux derives cyclopentaniques, leur procede de preparation et leur application comme medicaments
US4045489A (en) * 1976-01-15 1977-08-30 International Flavors & Fragrances Inc. Process for producing cis-jasmone
CH616077A5 (de) * 1976-06-30 1980-03-14 Firmenich & Cie
JPS5432444A (en) * 1977-08-12 1979-03-09 Otsuka Chem Co Ltd Preparation of cis-2-pentene derivative
US4294863A (en) * 1979-12-21 1981-10-13 International Flavors & Fragrances Inc. Flavoring with mixture of nor-methyl jasmonate and dihydro-nor-methyl jasmonate
US5235110A (en) * 1989-05-23 1993-08-10 Nippon Zeon Co., Ltd. Fragrant composition
ES2095521T3 (es) * 1992-07-20 1997-02-16 Firmenich & Cie Procedimiento para la preparacion de 3-oxo-2-pentil-1-ciclopenteno acetados de alquilo.
US5300489A (en) * 1993-06-11 1994-04-05 International Flavors & Fragrances Inc. Fragrance use of dihydromethyl jasmonic acid
US5436226A (en) * 1993-11-03 1995-07-25 The United States Of America, As Represented By The Secretary Of Agriculture Natural suppression of sprouting in stored potatoes using jasmonates

Also Published As

Publication number Publication date
WO1996000206A1 (fr) 1996-01-04
EP0715615A1 (de) 1996-06-12
DE69505226D1 (de) 1998-11-12
JPH09502459A (ja) 1997-03-11
US5728866A (en) 1998-03-17
JP3053872B2 (ja) 2000-06-19
EP0715615B1 (de) 1998-10-07

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