title: A convenient method for synthesis of enantiomerically enriched methylphenidate from N-methoxycarbonylpiperidine.
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.
authors.affiliation: Institute for Fundamental Research of Organic Chemistry, Kyushu University, Fukuoka, Japan. matumura@ms.ifoc.kyushu-u.ac.jp
authors.forename: Y
authors.initials: Y
authors.lastname: Matsumura
authors.forename: Y
authors.initials: Y
authors.lastname: Kanda
authors.forename: K
authors.initials: K
authors.lastname: Shirai
authors.forename: O
authors.initials: O
authors.lastname: Onomura
authors.forename: T
authors.initials: T
authors.lastname: Maki
mesh_terms: D018663:Adrenergic Agents / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D008774:Methylphenidate / Q000138:chemical synthesis*; D010880:Piperidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D018663:Adrenergic Agents; C410442:N-methoxycarbonylpiperidine; D010880:Piperidines; D008774:Methylphenidate