Title:
METHOD FOR PRODUCING (S)-2-(5-CHLORO-2-NITROPHENYL)-4-CYCLOPROPYL-1,1,1-TRIFLUOROBUT-3-YNE-2-OL
Document Type and Number:
WIPO Patent Application WO/2015/129630
Kind Code:
A1
Abstract:
[Problem] To provide a novel method for producing (S)-2-(5-chloro-2-nitrophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yne-2-ol. [Solution] An alkynyl ketone represented by belowmentioned formula (1) is reacted with (trifluoromethyl) trimethylsilane in a solvent in the presence of a basic group and a catalytic amount of a cinchona alkaloid phase transfer catalyst represented by belowmentioned general formula (3), (4), (5), or (6). (In the formulas, R1, R2, R3, R4 and X represent the meaning set forth in claim 1.)
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Inventors:
OKUSU SATOSHI (JP)
TOKUNAGA ETSUKO (JP)
SHIBATA NORIO (JP)
TOKUNAGA ETSUKO (JP)
SHIBATA NORIO (JP)
Application Number:
PCT/JP2015/055060
Publication Date:
September 03, 2015
Filing Date:
February 23, 2015
Export Citation:
Assignee:
NAGOYA INST TECHNOLOGY (JP)
International Classes:
C07C201/12; B01J31/02; C07C205/26; C07D453/04; A61K31/536; A61P31/18; A61P43/00; C07B53/00; C07B61/00
Foreign References:
| JP2014001177A | 2014-01-09 | |||
| JP2009215196A | 2009-09-24 | |||
| JP2005306769A | 2005-11-04 |
Other References:
SATOSHI OKUSU ET AL.: "Asymmetric Synthesis of Efavirenz via Organocatalyzed Enantioselective Trifluoromethylation", ASIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 4, pages 449 - 452
HIROYUKI KAWAI ET AL.: "A New Synthetic Approach to Efavirenz through Enantioselective Trifluoromethylation by Using the Ruppert- Prakash Reagent", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 30, 2011, pages 5959 - 5961
HIROYUKI KAWAI ET AL.: "Organocatalytic Asymmetric Synthesis of Trifluoromethyl- substituted Diarylpyrrolines: Enantioselective Conjugate Cyanation of beta-Aryl-beta- trifluoromethyl-disubstituted Enones", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 51, no. 20, 2012, pages 4959 - 4962, XP055044598, DOI: doi:10.1002/anie.201201278
XIAOLEI HU ET AL.: "Cinchona alkaloid-derived quaternary ammonium salt combined with NaH: a facile catalyst system for the asymmetric trifluoromethylation of ketones", TETRAHEDRON LETTERS, vol. 50, no. 30, 2009, pages 4378 - 4380
HIROYUKI KAWAI ET AL.: "A New Synthetic Approach to Efavirenz through Enantioselective Trifluoromethylation by Using the Ruppert- Prakash Reagent", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 30, 2011, pages 5959 - 5961
HIROYUKI KAWAI ET AL.: "Organocatalytic Asymmetric Synthesis of Trifluoromethyl- substituted Diarylpyrrolines: Enantioselective Conjugate Cyanation of beta-Aryl-beta- trifluoromethyl-disubstituted Enones", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 51, no. 20, 2012, pages 4959 - 4962, XP055044598, DOI: doi:10.1002/anie.201201278
XIAOLEI HU ET AL.: "Cinchona alkaloid-derived quaternary ammonium salt combined with NaH: a facile catalyst system for the asymmetric trifluoromethylation of ketones", TETRAHEDRON LETTERS, vol. 50, no. 30, 2009, pages 4378 - 4380
Attorney, Agent or Firm:
YOU-I Patent Firm (JP)
Patent business corporation ゆうあい patent firm (JP)
Patent business corporation ゆうあい patent firm (JP)
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