Title:
METHOD FOR PREPARING (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACID AND DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2019/184936
Kind Code:
A1
Abstract:
Disclosed in the present invention is a method for preparing (S)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and a derivative thereof. The method comprises: by using racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (1) or racemic 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (2) as a substrate, stereoselectively catalyzing an R-type isomer by means of D-amino acid oxidase, and generating a corresponding imidic acid by means of oxidative dehydrogenation, an S-type isomer being not catalyzed but retained in the reaction system; and generating a racemic substrate from the imidic acid under the action of an imidic acid reducing agent, and then stereoselectively catalyzing an R-type isomer in the racemic substrate under the action of D-amino acid oxidase, so as to prepare an S-type isomer. According to the method of the present invention, the yield can reach 75%-97.4%, and the ee value is greater than 99%. Furthermore, the method has the features such as mild reaction conditions, strong stereoselectivity, high reaction efficiency, high yield, and relatively simple process.
Inventors:
WU JIANPING (CN)
JU SHUYUN (CN)
SHI JUNWEI (CN)
YANG LIRONG (CN)
QIAN MINGXIN (CN)
JU SHUYUN (CN)
SHI JUNWEI (CN)
YANG LIRONG (CN)
QIAN MINGXIN (CN)
Application Number:
PCT/CN2019/079814
Publication Date:
October 03, 2019
Filing Date:
March 27, 2019
Export Citation:
Assignee:
TONGLI BIOMEDICAL CO LTD (CN)
UNIV ZHEJIANG (CN)
UNIV ZHEJIANG (CN)
International Classes:
C12P41/00; C07D217/16; C12P13/04
Foreign References:
| CN104557911A | 2015-04-29 | |||
| US20110086396A1 | 2011-04-14 | |||
| CN101194020A | 2008-06-04 |
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT & TRADEMARK AGENCY LTD. (CN)
Download PDF: