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A convenient method for synthesis of enantiomerically enriched methylphenidate from N-methoxycarbonylpiperidine
Y Matsumura1, Y Kanda, K Shirai
1Institute for Fundamental Research of Organic Chemistry, Kyushu University, Fukuoka, Japan. matumura@ms.ifoc.kyushu-u.ac.jp
Organic Letters
|May 24, 2000
Abstract:
[formula: see text] This report describes a new method to prepare optically active methylphenidate starting from piperidine. The method consists of a transformation of N-methoxycarbonylpiperidine to the corresponding alpha-methoxylated carbamate I by utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides II to produce optically active methylphenidate derivatives III with high stereoselectivities, threo-(2R,2'R)-Methylphenidate (IV; Ar = Ph; Ritalin) was easily prepared from III in three steps.