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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 14
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Original Articles

Concise and facile synthesis of (R,R)-dexmethylphenidate hydrochloride and its three stereoisomers

Chunzheng LiShanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, P. R. China;School of Engineering, China Pharmaceutical University, Nanjing, P. R. China
,
Yuanbo JiShanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, P. R. China;School of Engineering, China Pharmaceutical University, Nanjing, P. R. China
,
Qing CaoShanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, P. R. China
,
Jianqi LiShanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, P. R. China
&
Bonan LiShanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, P. R. ChinaCorrespondence[email protected]
Pages 1301-1306 | Received 28 Nov 2016, Published online: 16 Jun 2017
 
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ABSTRACT

A new and concise route is reported for the first time for the preparation of four stereoisomers of dexmethylphenidate hydrochloride starting from a single reactant, 2-benzyolpyridine, through an eight-step reaction process, which includes hydrogenation, protection, oxidation, chiral separation, Wittig reaction, hydroboration, pyridinium dichromate oxidation, and methyl esterification. The absolute configuration of the two chiral centers of each stereoisomer was confirmed by X-ray and chiral HPLC analyses.

GRAPHICAL ABSTRACT

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