Title:
PROCESS FOR UNPROTECTED ASYMMETRIC PREPARATION OF NICOTINE
Document Type and Number:
WIPO Patent Application WO/2023/206665
Kind Code:
A1
Abstract:
The present invention relates to a process for unprotected asymmetric preparation of nicotine. Specifically, optically pure nicotine is prepared from a nicotinate as the starting material through four reactions, wherein the preparation of a chiral alcohol intermediate compound with high optical activity by means of asymmetric catalytic reduction is a key step of the method. The method features high atom economy, high reactivity, high enantioselectivity of chiral products, short reaction procedures, cost-efficient starting materials, environmental conservation, the absence of contaminants, and ease of scale-up for industrial production.
Inventors:
LANG QIWEI (CN)
DING XIAOBING (CN)
GAO SHUANG (CN)
DING XIAOBING (CN)
GAO SHUANG (CN)
Application Number:
PCT/CN2022/093868
Publication Date:
November 02, 2023
Filing Date:
May 19, 2022
Export Citation:
Assignee:
SHENZHEN CATALYST TECH CO LTD (CN)
International Classes:
C07D213/30; B01J31/24; C07B53/00; C07D401/04
Foreign References:
| US20030166978A1 | 2003-09-04 | |||
| JPH06157459A | 1994-06-03 | |||
| CN114874134A | 2022-08-09 | |||
| CN105732725A | 2016-07-06 | |||
| CN106632511A | 2017-05-10 | |||
| CN107722068A | 2018-02-23 | |||
| CN112300219A | 2021-02-02 | |||
| CN114478362A | 2022-05-13 | |||
| CN113527187A | 2021-10-22 |
Other References:
HUANG, KUN ET AL.: "A New and Efficient Approach to the Synthesis of Nicotine and Anabasine Analogues", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 46, no. 6, 6 November 2009 (2009-11-06), XP093022372, DOI: 10.1002/jhet.233
DATABASE Registry CAS; 5 December 2021 (2021-12-05), ANONYMOUS : "1,4-Butanediol, 1-(3-pyridinyl)-, (1S)-", XP093105584, retrieved from STNext Database accession no. 2741216-80-6
MATHARU, D. S. ET AL.: "A Stereochemically Well-Defined Rhodium(III) Catalyst for Asymmetric Transfer Hydrogenation of Ketones", ORGANIC LETTERS, vol. 7, no. 24, 2 November 2005 (2005-11-02), XP002634538, DOI: 10.1021/ol052559f
WU WEILONG, XIE YUN, LI PAN, LI XIUXIU, LIU YUANHUA, DONG XIU-QIN, ZHANG XUMU: "Asymmetric hydrogenation of α-hydroxy ketones with an iridium/f-amphox catalyst: efficient access to chiral 1,2-diols", ORGANIC CHEMISTRY FRONTIERS, vol. 4, no. 4, 1 January 2017 (2017-01-01), pages 555 - 559, XP093105196, DOI: 10.1039/C6QO00810K
TOUGE, TAICHIRO; HAKAMATA, TOMOHIKO; NARA, HIDEKI; KOBAYASHI, TOHRU; SAYO, NOBORU; SAITO, TAKAO; KAYAKI, YOSHIHITO; IKARIYA, TAKAO: "Oxo-Tethered Ruthenium(II) Complex as a Bifunctional Catalyst for Asymmetric Transfer Hydrogenation and H2 Hydrogenation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 133, no. 38, 28 September 2011 (2011-09-28), pages 14960 - 14963, XP009152861, ISSN: 0002-7863, DOI: 10.1021/ja207283t
DATABASE Registry CAS; 5 December 2021 (2021-12-05), ANONYMOUS : "1,4-Butanediol, 1-(3-pyridinyl)-, (1S)-", XP093105584, retrieved from STNext Database accession no. 2741216-80-6
MATHARU, D. S. ET AL.: "A Stereochemically Well-Defined Rhodium(III) Catalyst for Asymmetric Transfer Hydrogenation of Ketones", ORGANIC LETTERS, vol. 7, no. 24, 2 November 2005 (2005-11-02), XP002634538, DOI: 10.1021/ol052559f
WU WEILONG, XIE YUN, LI PAN, LI XIUXIU, LIU YUANHUA, DONG XIU-QIN, ZHANG XUMU: "Asymmetric hydrogenation of α-hydroxy ketones with an iridium/f-amphox catalyst: efficient access to chiral 1,2-diols", ORGANIC CHEMISTRY FRONTIERS, vol. 4, no. 4, 1 January 2017 (2017-01-01), pages 555 - 559, XP093105196, DOI: 10.1039/C6QO00810K
TOUGE, TAICHIRO; HAKAMATA, TOMOHIKO; NARA, HIDEKI; KOBAYASHI, TOHRU; SAYO, NOBORU; SAITO, TAKAO; KAYAKI, YOSHIHITO; IKARIYA, TAKAO: "Oxo-Tethered Ruthenium(II) Complex as a Bifunctional Catalyst for Asymmetric Transfer Hydrogenation and H2 Hydrogenation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 133, no. 38, 28 September 2011 (2011-09-28), pages 14960 - 14963, XP009152861, ISSN: 0002-7863, DOI: 10.1021/ja207283t
Attorney, Agent or Firm:
GUANGDONG JINTAI ZHIHUI PATENT & TRADEMARK AGENCY (GENERAL PARTNERSHIP) (CN)
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