Stereochemistry of the asymmetric reduction of (1′s)-1,3-dimethyl-4(1′-phenylethylimino)piperidine

Autor: Grishina, G. V., Gaidarova, E. L., Luk'yanenko, E. R., Borisenko, A. A.
Zdroj: Chemistry of Heterocyclic Compounds; February 1996, Vol. 32 Issue: 2 p194-196, 3p
Abstrakt: The stereochemistry of the asymmetric reduction of the imine obtained from 1,3-dimethylpiperidin-4-one and (S)-a-phenylethylamine has been studied. It is shown that hydride reduction of imine 1 by sodium borohydride in methanol is asymmetric and gives the cis and trans diastereomeric pair 1,3-dimethyl-4-(a-phenyl-ethylamino) piperidine in the ratio 3:1. Using sodium in isopropanol gives only one trans diastereomeric pair.1H NMR has been used to identify the stereochemical structure and diastereomer excess of the cis and trans isomers of 1,3-dimethyl-4-(a-phenylethylamino)piperidine which had been separated by column chromatography.
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