Title:
EPOXY COMPOUND PRODUCTION METHOD
Document Type and Number:
WIPO Patent Application WO/2018/097150
Kind Code:
A1
Abstract:
With a step in which a phosphoric acid compound and/or a phosphonic acid compound, a group 6 metal compound, a phase transfer catalyst, and hydrogen peroxide are added to and reacted with 3-cyclopentene in which the 1-position is substituted by a C1-C6 alkoxycarbonyl group, a benzyloxycarbonyl group, a C1-C6 alkylcarbonyl group, a benzyloxycarbonyl group, a C1-C6 alkyl group or a benzoyl group (these substituents may be further substituted by specific substituents), this production method produces a corresponding epoxy compound. From a 3-cyclopentene in which the 1-position is monosubstituted with a specific substituent, a corresponding epoxy compound with high stereoselectivity can be produced.
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Inventors:
TSUCHIYA HIDEYOSHI (JP)
Application Number:
PCT/JP2017/041914
Publication Date:
May 31, 2018
Filing Date:
November 22, 2017
Export Citation:
Assignee:
TEIJIN PHARMA LTD (JP)
International Classes:
C07D301/12; B01J31/02; C07D303/40
Domestic Patent References:
| WO2007081889A2 | 2007-07-19 |
Foreign References:
| JP2008094741A | 2008-04-24 |
Other References:
MARTINEZ, L. E. ET AL.: "Highly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition Metal Catalysis", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 22, 1996, pages 7963 - 7966, XP002041317, ISSN: 0022-3263
ENKVIST, E. ET AL.: "Carbocyclic 3'-deoxyadenosine-based highly potent bisubstrate-analog inhibitor of basophilic protein kinases", BIORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 17, 2007, pages 5336 - 5339, XP022249711, ISSN: 0960-894X
WHITE, D. E ET AL.: "Abroadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions", TETRAHEDRON, vol. 70, no. 27-28, 2014, pages 4165 - 4180, XP029026739, ISSN: 0040-4020
GRELLEPOIS, F. ET AL.: "1-(Trifluoromethyl) cyclopent-3-enecarboxylic Acid Derivatives: Platforms for Bifunctional Cyclic Trifluoromethyl BuildingBlocks", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2012, no. 3, 2012, pages 509 - 517, XP055487918, ISSN: 1099-0690
GIANNELLA, M. ET AL.: "Synthesis and muscarinic properties of (1S*,3R*,5R*)-trimethyl(1-methyl-6-oxabicyclo[3.1. 0]hex-3-yl)methyl ammonium iodide", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 42, no. 6, 1994, pages 1286 - 1290, XP055487922, ISSN: 0009-2363
CRESSWELL, A. J. ET AL.: "Catalytic, stereospecific syn-dichlorination of alkenes", NATURE CHEMISTRY, vol. 7, no. 2, 2015, pages 146 - 152, XP055487923, ISSN: 1755-4330
ENKVIST, E. ET AL.: "Carbocyclic 3'-deoxyadenosine-based highly potent bisubstrate-analog inhibitor of basophilic protein kinases", BIORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 17, 2007, pages 5336 - 5339, XP022249711, ISSN: 0960-894X
WHITE, D. E ET AL.: "Abroadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions", TETRAHEDRON, vol. 70, no. 27-28, 2014, pages 4165 - 4180, XP029026739, ISSN: 0040-4020
GRELLEPOIS, F. ET AL.: "1-(Trifluoromethyl) cyclopent-3-enecarboxylic Acid Derivatives: Platforms for Bifunctional Cyclic Trifluoromethyl BuildingBlocks", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2012, no. 3, 2012, pages 509 - 517, XP055487918, ISSN: 1099-0690
GIANNELLA, M. ET AL.: "Synthesis and muscarinic properties of (1S*,3R*,5R*)-trimethyl(1-methyl-6-oxabicyclo[3.1. 0]hex-3-yl)methyl ammonium iodide", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 42, no. 6, 1994, pages 1286 - 1290, XP055487922, ISSN: 0009-2363
CRESSWELL, A. J. ET AL.: "Catalytic, stereospecific syn-dichlorination of alkenes", NATURE CHEMISTRY, vol. 7, no. 2, 2015, pages 146 - 152, XP055487923, ISSN: 1755-4330
Attorney, Agent or Firm:
TAMEYAMA Taro (JP)
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