Title:
METHOD FOR SYNTHESIZING TRANYLCYPROMINE INTERMEDIATE
Document Type and Number:
WIPO Patent Application WO/2021/047166
Kind Code:
A1
Abstract:
The present invention is applicable to the technical field of pharmaceutical synthesis, and provides a method for synthesizing a tranylcypromine intermediate. The method comprises subjecting a substituted aromatic ketone or a polysubstituted aromatic ketone to a substitution reaction under the action of sodium nitrite, sodium iodide and a reaction solvent to synthesize compound I; subjecting compound I to a copper hydrogen catalysis reaction under the action of a metal precursor, a ligand and a catalyst to produce compound II; causing compound II to produce compound III under the action of DIAD and triphenylphosphine; and causing compound III to produce a tranylcypromine intermediate under the action of zinc powder or iron powder. In the synthesis method, the raw materials used are safe and low in cost, and the yield and selectivity are extremely high, while the reaction cost is reduced; and in the process of synthesizing a chiral alcohol, only low-cost metal precursors and ligands are needed, without it being necessary to use expensive chiral oxazaborolidine and a toxic borane dimethyl sulfide compound; and catalysis is completed with a small equivalent of the catalyst. The invention has an extremely high industrialization value, and meets market demands.
Inventors:
ZHAO JINHUI (CN)
ZHENG YONGPENG (CN)
WANG BAIGUI (CN)
ZHENG YONGPENG (CN)
WANG BAIGUI (CN)
Application Number:
PCT/CN2020/082636
Publication Date:
March 18, 2021
Filing Date:
March 31, 2020
Export Citation:
Assignee:
SHENZHEN CATALYS TECH CO LTD (CN)
International Classes:
C07C45/46
Domestic Patent References:
| WO2011132083A2 | 2011-10-27 |
Foreign References:
| CN103429576A | 2013-12-04 | |||
| CN103508899A | 2014-01-15 | |||
| EP2589587A1 | 2013-05-08 |
Other References:
ZENG WEIJUN, TAN XUEFENG, YU YANG, CHEN GEN-QIANG, ZHANG XUMU: "Copper-Catalyzed Asymmetric Hydrosilylation of β-Nitroethyl Aryl Ketones", ORGANIC LETTERS ., AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 3, 7 February 2020 (2020-02-07), US, pages 858 - 862, XP055792344, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.9b04339
ZHOU JI-NING, FANG QIANG, HU YI-HU, YANG LI-YAO, WU FEI-FEI, XIE LIN-JIE, WU JING, LI SHIJUN: "Copper(ii)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 12, no. 6, 3 December 2014 (2014-12-03), GB, pages 1009 - 1017, XP055792342, ISSN: 1477-0520, DOI: 10.1039/c3ob42214c
ZHOU JI-NING, FANG QIANG, HU YI-HU, YANG LI-YAO, WU FEI-FEI, XIE LIN-JIE, WU JING, LI SHIJUN: "Copper(ii)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 12, no. 6, 3 December 2014 (2014-12-03), GB, pages 1009 - 1017, XP055792342, ISSN: 1477-0520, DOI: 10.1039/c3ob42214c
Attorney, Agent or Firm:
SHENZHEN LANFENG SHENGSHI INTELLECTUAL PROPERTY AGENCY CO., LTD (CN)
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