Asymmetric Synthesis. 39.1 Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine

• Published in: Journal of Organic Chemistry, vol. 61, num. 19, p. 6700-6705
• Publication date: 1996

The asym. synthesis of a series of 2-piperidinealkanamines starting from (-)-2-cyano-6-phenyloxazolopiperidine was [i.e., [3R-(3alpha ,5beta ,8abeta )]-hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile] (I) as described. LiAlH4 redn. of I followed by hydrogenolysis gave (-)-2-piperidinemethanamine dihydrochloride (II). Addn. of lithium derivs. to the cyano group of I resulted in the formation of intermediate imino bicyclic systems which could be diastereoselectively reduced to substituted diamino alcs. The addn. of an excess of PhLi to I in the presence of LiBr gave a disubstituted amine, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine. [on SciFinder (R)]

Keywords: Asymmetric synthesis and induction (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile) ; piperidinemethanamine asym synthesis; aminomethyl piperidine asym synthesis

Note:

CAN 125:247551

27-16

Heterocyclic Compounds (One Hetero Atom)

Faculte des Sciences Pharmaceutiques et Biologiques,Universite Rene Descartes,Paris,Fr.

Journal

0022-3263

written in English.

88056-92-2 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile); 153918-98-0P; 156350-14-0P; 181872-15-1P; 181872-19-5P; 181872-20-8P; 181872-21-9P; 181872-22-0P; 181872-23-1P; 181872-24-2P; 181872-26-4P; 181872-28-6P; 181872-29-7P; 181872-31-1P; 181872-32-2P; 181872-33-3P; 182074-39-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile); 126811-36-7P; 153918-99-1P; 181872-10-6P; 181872-12-8P; 181872-17-3P; 181872-25-3P; 181872-27-5P; 181872-30-0P; 181872-34-4P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile)

Reference

• EPFL-ARTICLE-158196
• doi:10.1021/jo960910s

Record created on 2010-11-25, modified on 2017-05-12