Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers

doi:10.6023/cjoc201603001

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2162-2167.DOI: 10.6023/cjoc201603001 Previous Articles Next Articles

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盐酸右哌甲酯及其光学异构体的合成

张飞龙^a,b, 李伯男^a,b, 孙媛媛^a,b, 李建其^a,b

a 中国医药工业研究总院上海医药工业研究院化学制药新技术中心上海 201203;
b 上海药物合成工艺过程工程技术研究中心上海 201203

收稿日期:2016-03-01 修回日期:2016-04-06 发布日期:2016-05-06
通讯作者: 李伯男, 李建其 E-mail:pkuthulbn@gmail.com;lijianqb@126.com
基金资助:
国家“十二五”科技重大专项（No.2014ZX09507006-002）和2016年上海市浦江人才计划（No.16PJ1432800）资助项目.

Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers

Zhang Feilong^a,b, Li Bonan^a,b, Sun Yuanyuana^a,b, Li Jianqi^a,b

a Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, Shanghai 201203;
b Shanghai Engineering Reseach Center of Pharmaceutical Process, Shanghai 201203

Received:2016-03-01 Revised:2016-04-06 Published:2016-05-06
Supported by:
Project supported by the National Science and Technology Major Project of Ministry of Science and Technology (No.2014ZX09507006-002) and the 2016 Shanghai Pujiang Talent Plan (No.16PJ1432800).

1. Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers.PDF(1201KB)

Abstract

For the purpose of quality control of demethylphenidate hydrochloride (1a), three related optical substances were synthesized and characterized. (S,S)-Methylphenidate hydrochloride (1b), (R,S)-methylphenidate hydrochloride (1c) and (S,R)-methylphenidate hydrochloride (1d) were synthesized via the same route with demethylphenidate hydrochloride but changing different intermediates or resolving agents. The structures of four optical isomers were tested by MS and NMR spectra, the chemical and optical purities were analyzed by HPLC spectra, the specific rotation values were also measured, the absolute configurations of compounds 1a and 1d were confirmed by X-ray study. The three optical isomers can be used as the reference substances of the related optical substances in the quality control of demethylphenidate hydrochloride.

Key words: demethylphenidate hydrochloride, related optical isomers, synthesis

Cite this article

Zhang Feilong, Li Bonan, Sun Yuanyuana, Li Jianqi. Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers[J]. Chin. J. Org. Chem., 2016, 36(9): 2162-2167.

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盐酸右哌甲酯及其光学异构体的合成

Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers

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