Chemical resolution on (±)1-(Benzamidomethyl)-1,2,3,4-tetrahydro-isoquinoline
- VernacularTitle:（±）1－［（苯甲酰氨基）甲基］－1，2，3，4－四氢异喹啉的化学拆分研究
- Author:
Xiaohong ZHENG
;
Jiezhong CHEN
;
Qingwei HU
;
Xiaojuan ZHANG
- Publication Type:Journal Article
- Keywords:
tetrahydroisoquinoline;
chemical resolution;
camphor sulfonic acid
- From:
Chinese Journal of Biochemical Pharmaceutics
2015;(8):170-172,175
- CountryChina
- Language:Chinese
-
Abstract:
Objective To obtain two types of optical isomers from 1-(Benzamidomethyl)-1,2,3,4-tetrahydro-isoquinoline (BTIQ). Methods ( ±) BTIQ as raw materials , optically pure camphor sulfonic acid as resolution agent was used and repeated resolution in acetone , And the resolution product was detected by specific optical rotation .The product of BTIQ was hydrolyzed , and the ratio of ATIQ was compared with that of the literature .ResuIts After two repeated chemical resolutions , the specific rotations of both enantiomers are no longer changed .It was showed that the products of higher optical purity.The specific rotation of both isomers are -35.65°(CH2Cl2, C=0.5)with the yield of 27.52%,and +35.17°(CH2Cl2, C =0.5) with the yield of 31.55% respectively.The specific rotation value of chiral 1,2,3,4-tetrahydroisoquino line ( ATIQ) which was the hydrolysis product of BTIQ consistent with values reported in the literature .ConcIusion The (-) BTIQ and ( +) BTIQ enantiomers were successfully obtained by the method of resolution , and the yield and optical purity of the obtained products are higher , laying the foundation for the further development of high efficiency , low toxicity of chiral schistosomicide ( praziquantel ) and other containing tetrahydroisoquinoline structure of chiral drugs .
