Citation: Zhang Feilong, Li Bonan, Sun Yuanyuana, Li Jianqi. Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2162-2167. doi: 10.6023/cjoc201603001 shu

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

Corresponding author: Li Bonan, pkuthulbn@gmail.com Li Jianqi, lijianqb@126.com
Received Date: 1 March 2016
Revised Date: 6 April 2016

Fund Project: the 2016 Shanghai Pujiang Talent Plan 16PJ1432800the National Science and Technology Major Project of Ministry of Science and Technology 2014ZX09507006-002

Figures(6)

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.
- demethylphenidate hydrochloride,
- related optical isomers,
- synthesis
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