Title:
METHOD FOR SYNTHESIZING (S)-NICOTINE
Document Type and Number:
WIPO Patent Application WO/2021/180019
Kind Code:
A1
Abstract:
Provided is a method for synthesizing (S)-nicotine, comprising: under the condition of a coenzyme circulation system, by using a coenzyme as a hydrogen donor, and by using imine reductase as a catalyst, catalyzing and reducing myosmine to (S)-nornicotine, and then subjecting (S)-nornicotine to a methylation reaction so as to obtain (S)-nicotine.
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Inventors:
LIN WENQING (CN)
ZHENG HONGJIE (CN)
CHEN ZENGCONG (CN)
ZHU JIANPING (CN)
YUE YONGTANG (CN)
HU JICHENG (CN)
WANG JIANCHONG (CN)
LI LINGYU (CN)
LIU XIAOBO (CN)
ZHENG HONGJIE (CN)
CHEN ZENGCONG (CN)
ZHU JIANPING (CN)
YUE YONGTANG (CN)
HU JICHENG (CN)
WANG JIANCHONG (CN)
LI LINGYU (CN)
LIU XIAOBO (CN)
Application Number:
PCT/CN2021/079492
Publication Date:
September 16, 2021
Filing Date:
March 08, 2021
Export Citation:
Assignee:
PORTON PHARMA SOLUTIONS LTD (CN)
International Classes:
C12P17/16; C07D401/04
Domestic Patent References:
| WO2014174505A2 | 2014-10-30 |
Foreign References:
| CN107406411A | 2017-11-28 | |||
| EP3653617A1 | 2020-05-20 | |||
| CN112409327A | 2021-02-26 | |||
| US20160326134A1 | 2016-11-10 | |||
| EP2487172A1 | 2012-08-15 |
Other References:
PEYTON JACOB: "Resolution of (±)-5-Bromonornicotine. Synthesis of (R)-and (S)-Nornicotine of High Enantiomeric Purity", THE JOURNAL OF ORGANIC CHEMISTRY, 1982, pages 4165 - 4167, XP055023791, DOI: 10.1021/jo00142a032
GUI GUODONG-WEI SUNSHUANG YANG ET AL.: "Iridium-Catalyzed Asymmetric Hydrogenation of 2-Pyridyl Cyclic Imines: A Highly Enantioselective Approach to Nicotine Derivatives", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, pages 90 - 93, XP055470306, DOI: 10.1021/ja511422q
TECK-PENG LOHJIAN-RONG ZHOUXU-RAN LIKENG-YEOW SIM: "A novel reductive aminocyclization for the syntheses of chiral pyrrolidines: stereoselective syntheses of (S)-nornicotine and 2-(2'-pyrrolidl)-pyridines", TETRAHEDRON LETTERS, 1999, pages 7847 - 7850, XP004180974, DOI: 10.1016/S0040-4039(99)01606-8
GUI GUODONG-WEI SUNSHUANG YANG ET AL.: "Iridium-Catalyzed Asymmetric Hydrogenation of 2-Pyridyl Cyclic Imines: A Highly Enantioselective Approach to Nicotine Derivatives", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, pages 90 - 93, XP055470306, DOI: 10.1021/ja511422q
TECK-PENG LOHJIAN-RONG ZHOUXU-RAN LIKENG-YEOW SIM: "A novel reductive aminocyclization for the syntheses of chiral pyrrolidines: stereoselective syntheses of (S)-nornicotine and 2-(2'-pyrrolidl)-pyridines", TETRAHEDRON LETTERS, 1999, pages 7847 - 7850, XP004180974, DOI: 10.1016/S0040-4039(99)01606-8
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