EA033302B9 - (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 - Google Patents

(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

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Publication number
EA033302B9
EA033302B9 EA201500665A EA201500665A EA033302B9 EA 033302 B9 EA033302 B9 EA 033302B9 EA 201500665 A EA201500665 A EA 201500665A EA 201500665 A EA201500665 A EA 201500665A EA 033302 B9 EA033302 B9 EA 033302B9
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EA
Eurasian Patent Office
Prior art keywords
trimetylpentadeca
trimetylpentadecan
trien
dien
mixture
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EA201500665A
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English (en)
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EA033302B1 (ru
EA201500665A1 (ru
Inventor
Вернер Бонрат
Томас Нечер
Джонатан Алан Медлок
Рене Тобиас Штемлер
Йоганнес Чуми
Герардус Карел Мария Верзейл
Андреас Хендрикус Мария Врис де
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ДСМ АйПи АССЕТС Б.В.
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Application filed by ДСМ АйПи АССЕТС Б.В. filed Critical ДСМ АйПи АССЕТС Б.В.
Publication of EA201500665A1 publication Critical patent/EA201500665A1/ru
Publication of EA033302B1 publication Critical patent/EA033302B1/ru
Publication of EA033302B9 publication Critical patent/EA033302B9/ru

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    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
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    • 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
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
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    • 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
    • C07C45/61—Preparation 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
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C45/67—Preparation 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
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    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
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Abstract

Изобретение относится к способу получения конкретного изомера (6R,10R)-6,10,14-триметилпентадекан-2-она многостадийным синтезом из смеси изомеров (5E,9E)-/(5E,9Z)-/(5Z,9E)- и (5Z,9Z)-6,10,14-триметилпентадека-5,9,13-триен-2-она или смеси (5E,9E)-/(5E,9Z)-/(5Z,9E)- и (5Z,9Z)-6,10,14-триметилпентадека-5,9-диен-2-она путем ассиметричной гидрогенизации молекулярным водородом в присутствии хирального комплекса иридия формулы (III), где группы и символы в формуле (III) имеют значения, которые определены в описании. Способ обладает большим полезным эффектом, поскольку предлагает эффективный путь получения желательного хирального продукта из смеси стереоизомеров исходного продукта.
EA201500665A 2012-12-18 2013-12-18 (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 EA033302B9 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12197812 2012-12-18
PCT/EP2013/077233 WO2014096098A1 (en) 2012-12-18 2013-12-18 (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one

Publications (3)

Publication Number Publication Date
EA201500665A1 EA201500665A1 (ru) 2015-12-30
EA033302B1 EA033302B1 (ru) 2019-09-30
EA033302B9 true EA033302B9 (ru) 2020-01-22

Family

ID=47458691

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EA201500665A EA033302B9 (ru) 2012-12-18 2013-12-18 (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

Country Status (8)

Country Link
US (1) US9611200B2 (ru)
EP (1) EP2935185B1 (ru)
JP (1) JP6582324B2 (ru)
CN (1) CN104854071B (ru)
BR (1) BR112015014423B1 (ru)
EA (1) EA033302B9 (ru)
MY (1) MY173272A (ru)
WO (1) WO2014096098A1 (ru)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014096065A1 (en) * 2012-12-18 2014-06-26 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
WO2014096106A1 (en) * 2012-12-18 2014-06-26 Dsm Ip Assets B.V. Using mixtures of e/z isomers to obtain quantitatively specific products by combined asymmetric hydrogenations
US9573872B2 (en) * 2012-12-18 2017-02-21 Dsm Ip Assets B.V. Using mixtures of E/Z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization
WO2017098050A1 (en) * 2015-12-11 2017-06-15 Dsm Ip Assets B.V. Process for the manufacture of 6,10,14-trimethylpentadecan-2-one, isophytol and alpha-tocopherol

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US4028385A (en) * 1974-09-02 1977-06-07 Kuraray Co., Ltd. Process for preparing stereospecific farnesylacetic acid and ester thereof
US5600015A (en) * 1992-04-16 1997-02-04 Hoffmann-La Roche Inc. Assymetric hydrogenation of isoprene derivatives
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EP2935181B1 (en) * 2012-12-18 2019-01-30 DSM IP Assets B.V. Efficient process of asymmetric hydrogenation of unsaturated ketones using additives
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WO2014096065A1 (en) * 2012-12-18 2014-06-26 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

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US4028385A (en) * 1974-09-02 1977-06-07 Kuraray Co., Ltd. Process for preparing stereospecific farnesylacetic acid and ester thereof
FR2302992A1 (fr) * 1974-09-10 1976-10-01 Kuraray Co Procede pour preparer des isomeres stereospecifiques de geranylacetone
US5600015A (en) * 1992-04-16 1997-02-04 Hoffmann-La Roche Inc. Assymetric hydrogenation of isoprene derivatives
WO2006066863A1 (en) * 2004-12-22 2006-06-29 Dsm Ip Assets B.V. Asymmetric hydrogenation of alkennes using chiral iridium complexes

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Publication number Publication date
EA033302B1 (ru) 2019-09-30
MY173272A (en) 2020-01-09
BR112015014423A2 (pt) 2017-07-11
US20150329456A1 (en) 2015-11-19
BR112015014423B1 (pt) 2020-12-01
JP2016506393A (ja) 2016-03-03
JP6582324B2 (ja) 2019-10-02
CN104854071A (zh) 2015-08-19
CN104854071B (zh) 2018-05-11
US9611200B2 (en) 2017-04-04
EP2935185A1 (en) 2015-10-28
EP2935185B1 (en) 2019-02-20
WO2014096098A1 (en) 2014-06-26
EA201500665A1 (ru) 2015-12-30

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