title: Asymmetric Synthesis. 39.(1) Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine.
abstract: The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH(4) reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).
authors.affiliation: Institut de Chimie des Substances Naturelles du CNRS 91198, Gif-sur-Yvette Cedex, France.
authors.forename: Olivier
authors.initials: O
authors.lastname: Froelich
authors.forename: Patrice
authors.initials: P
authors.lastname: Desos
authors.forename: Martine
authors.initials: M
authors.lastname: Bonin
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Quirion
authors.forename: Henri-Philippe
authors.initials: HP
authors.lastname: Husson
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu