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A Convenient Method for Synthesis of Enantiomerically Enriched Methylphenidate from N-Methoxycarbony

A Convenient Method for Synthesis of Enantiomerically Enriched Methylphenidate from N-Methoxycarbony

  1. Dr. Jackal
    Yoshihiro Matsumura, Yasuhisa Kanda, Kimihiro Shirai, Osamu Onomura, and Toshihide Maki

    Org. Lett., 1999, 1 (2), pp 175–178
    DOI: 10.1021/ol9905046
    Publication Date (Web): June 4, 1999

    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 α-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; Arhttp://pubs.acs.org/entityImage/legacy/dbd.gifPh; Ritalin) was easily prepared from III in three steps.