EA033435B1 - Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации - Google Patents

Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации

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Publication number
EA033435B1
EA033435B1 EA201500662A EA201500662A EA033435B1 EA 033435 B1 EA033435 B1 EA 033435B1 EA 201500662 A EA201500662 A EA 201500662A EA 201500662 A EA201500662 A EA 201500662A EA 033435 B1 EA033435 B1 EA 033435B1
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EA
Eurasian Patent Office
Prior art keywords
iii
isomers
isomerization
mixtures
asymmetric hydrogenation
Prior art date
Application number
EA201500662A
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English (en)
Other versions
EA201500662A1 (ru
Inventor
Werner Bonrath
Thomas Netscher
Jonathan Alan Medlock
Rene Tobias Stemmler
Gerardus Karel Maria Verzijl
Vries Andreas Hendrikus Maria De
Original Assignee
Dsm Ip Assets Bv
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Application filed by Dsm Ip Assets Bv filed Critical Dsm Ip Assets Bv
Publication of EA201500662A1 publication Critical patent/EA201500662A1/ru
Publication of EA033435B1 publication Critical patent/EA033435B1/ru

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/18Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/20Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/60Preparation of compounds having groups or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Pyrane Compounds (AREA)

Abstract

Изобретение касается способа получения соединений, содержащих стереогенные центры, из смеси E/Z-изомеров ненасыщенных соединений, содержащих прохиральные двойные связи, путем гидрогенизации соответствующего изомера молекулярным водородом в присутствии хирального комплекса иридия формулы (III), выбираемой из формул (III-C), (III-D) и (III-F), где группы и символы в указанных формулах имеют значения, которые определены в настоящем описании. Продукты гидрогенизации обладают заданной конфигурацией по стереогенным центрам. Способ включает стадию асимметрической гидрогенизации и стадию изомеризации. Способ дает большие преимущества тем, что в нем из смеси стереоизомеров исходного соединения эффективно образуется требуемый хиральный продукт.
EA201500662A 2012-12-18 2013-12-18 Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации EA033435B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12197857 2012-12-18
PCT/EP2013/077246 WO2014096107A1 (en) 2012-12-18 2013-12-18 Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization

Publications (2)

Publication Number Publication Date
EA201500662A1 EA201500662A1 (ru) 2015-12-30
EA033435B1 true EA033435B1 (ru) 2019-10-31

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EA201500662A EA033435B1 (ru) 2012-12-18 2013-12-18 Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации

Country Status (8)

Country Link
US (1) US9573872B2 (ru)
EP (1) EP2935189B1 (ru)
JP (1) JP6406676B2 (ru)
CN (1) CN104884420A (ru)
BR (1) BR112015014204B1 (ru)
EA (1) EA033435B1 (ru)
ES (1) ES2739229T3 (ru)
WO (1) WO2014096107A1 (ru)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA033302B9 (ru) * 2012-12-18 2020-01-22 ДСМ АйПи АССЕТС Б.В. (6r,10r)-6,10,14-триметилпентадекан-2-он, получаемый из 6,10,14-триметилпентадека-5,9,13-триен-2-она или 6,10,14-триметилпентадека-5,9-диен-2-она
US9452961B2 (en) * 2012-12-18 2016-09-27 Dsm Ip Assets B.V. (6R,10R)-6,10,14-trimetylpentadecan-2-one prepared from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one
BR112015014284B1 (pt) * 2012-12-18 2020-01-21 Dsm Ip Assets Bv processo de hidrogenação assimétrica de cetais e acetais, processo para a fabricação de aldeídos ou cetonas, composição e uso da mesma
JP6390048B2 (ja) * 2012-12-18 2018-09-19 ディーエスエム アイピー アセッツ ビー.ブイ.Dsm Ip Assets B.V. 組み合わされた不斉水素化によって特定の生成物を定量的に得るためのe/z異性体の混合物の使用
MX2020008509A (es) * 2018-02-13 2020-09-25 Basf Se Metodo para la isomerizacion de un acido carboxilico 3-(z)-insaturado en el isomero 3-(e).

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2302996A1 (fr) * 1974-09-02 1976-10-01 Kuraray Co Procede pour preparer des isomeres stereospecifiques de l'acide farnesylacetique, de ses esters et de leurs derives
EP1179531A1 (en) * 2000-08-11 2002-02-13 Aventis Animal Nutrition S.A. Intermediates for use in the preparation of vitamin E
WO2006066863A1 (en) * 2004-12-22 2006-06-29 Dsm Ip Assets B.V. Asymmetric hydrogenation of alkennes using chiral iridium complexes

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE634738A (ru) 1962-07-11 1900-01-01
DE2455975A1 (de) * 1973-11-30 1975-07-10 Firmenich & Cie Verwendung von neuen acetalen als riech- und geschmacksstoffe
GB1479272A (en) 1974-12-23 1977-07-13 Kuraray Co Process for preparing a stereospecific farnesol
JPS6036479A (ja) * 1983-08-08 1985-02-25 Kotobuki Seiyaku Kk 1,3−ジオキサン誘導体、本化合物を有効成分とする抗潰瘍剤及びその製造方法
JP2771866B2 (ja) * 1989-11-01 1998-07-02 エーザイ株式会社 不飽和テルペン類の製造方法
JP3725233B2 (ja) * 1995-04-18 2005-12-07 株式会社カネボウ化粧品 トレハロース誘導体及び界面活性剤
US5908957A (en) 1997-02-14 1999-06-01 Roche Vitamins Inc. Isomerization process
CN100564372C (zh) 2004-08-19 2009-12-02 帝斯曼知识产权资产管理有限公司 用于精馏高沸点的对空气和/或温度敏感的有用产品的混合物的方法
CN101565366B (zh) * 2008-04-25 2013-04-17 浙江九洲药业股份有限公司 铱络合物在不饱和羧酸不对称催化氢化中的应用
WO2010006954A1 (en) * 2008-07-15 2010-01-21 Dsm Ip Assets B.V. Novel n-substituted beta-amino acid esters
EP2543437A4 (en) * 2010-03-04 2014-09-03 Takasago Perfumery Co Ltd HOMOGENEOUS ASYMMETRIC HYDROGENATION CATALYST
JP6390048B2 (ja) * 2012-12-18 2018-09-19 ディーエスエム アイピー アセッツ ビー.ブイ.Dsm Ip Assets B.V. 組み合わされた不斉水素化によって特定の生成物を定量的に得るためのe/z異性体の混合物の使用
EA033302B9 (ru) * 2012-12-18 2020-01-22 ДСМ АйПи АССЕТС Б.В. (6r,10r)-6,10,14-триметилпентадекан-2-он, получаемый из 6,10,14-триметилпентадека-5,9,13-триен-2-она или 6,10,14-триметилпентадека-5,9-диен-2-она
US9452961B2 (en) * 2012-12-18 2016-09-27 Dsm Ip Assets B.V. (6R,10R)-6,10,14-trimetylpentadecan-2-one prepared from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2302996A1 (fr) * 1974-09-02 1976-10-01 Kuraray Co Procede pour preparer des isomeres stereospecifiques de l'acide farnesylacetique, de ses esters et de leurs derives
EP1179531A1 (en) * 2000-08-11 2002-02-13 Aventis Animal Nutrition S.A. Intermediates for use in the preparation of vitamin E
WO2006066863A1 (en) * 2004-12-22 2006-06-29 Dsm Ip Assets B.V. Asymmetric hydrogenation of alkennes using chiral iridium complexes

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ARAVAMUDAN S. GOPALAN, ROBERT PRIETO, BRITTA MUELLER, DAVID PETERS: "Polyene cyclizations using mercury (II) triflate-N,N-dimethylaniline complex - participation by internal nucleophiles", TETRAHEDRON LETTERS, PERGAMON, vol. 33, no. 13, 1 March 1992 (1992-03-01), pages 1679 - 1682, XP055058597, ISSN: 00404039, DOI: 10.1016/S0040-4039(00)91704-0 *
CHEMICAL ABSTRACTS, 7 January 1997, Columbus, Ohio, US; IKEMOTO TAKESHI, ET AL: "Preparation of 4,6-O-alkylidene-.alpha.,.alpha.-trehalose as surfactants" XP002697173 *
JUSTICIA, J. OLTRA, J.E. CUERVA, J.M.: "Palladium mediated C-H activation in the field of terpenoids: synthesis of rostratone", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 22, 24 May 2004 (2004-05-24), AMSTERDAM, NL, pages 4293 - 4296, XP004506345, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2004.04.005 *
TOSHIO KUBOTA, SATOSHI MIYASHITA, TOMOYA KITAZUME, NOBUO ISHIKAWA: "Novel synthetic reactions using bis(2,2,2-trifluoroethoxy)triphenylphosphorane", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY �ETC.|, vol. 45, no. 25, 1 December 1980 (1980-12-01), pages 5052 - 5057, XP055105066, ISSN: 00223263, DOI: 10.1021/jo01313a008 *
YOSHIHARU MATSUBARA; TANIICHIRO YAMAGA; KOJI TSUJIKAWA; SHOJI WAKABAYASHI: "Synthesis of New Acetals and their Derivatives from Terpene Aldehyde and Alcohol", YUKI GOSEI KAGAKU KYOKAISHI - JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY. JAPAN., YUKI GOSEI KAGAKU KAOKAI, TOKYO., JP, vol. 28, no. 8, 1 January 1970 (1970-01-01), JP, pages 849 - 852, XP002694891, ISSN: 0037-9980, DOI: 10.5059/yukigoseikyokaishi.28.849 *

Also Published As

Publication number Publication date
EP2935189B1 (en) 2019-06-12
JP6406676B2 (ja) 2018-10-17
BR112015014204B1 (pt) 2021-03-30
US20160185702A1 (en) 2016-06-30
EA201500662A1 (ru) 2015-12-30
US9573872B2 (en) 2017-02-21
BR112015014204A2 (pt) 2017-07-11
ES2739229T3 (es) 2020-01-29
CN104884420A (zh) 2015-09-02
JP2016505568A (ja) 2016-02-25
WO2014096107A1 (en) 2014-06-26
EP2935189A1 (en) 2015-10-28

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Designated state(s): AM AZ BY KZ KG TJ TM RU