Chinese Journal of Organic Chemistry >
Synthesis of Demethylphenidate Hydrochloride and Its Related Optical Isomers
Received date: 2016-03-01
Revised date: 2016-04-06
Online 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).
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.
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
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