Stereochemistry of the asymmetric reduction of (1′<i>S</i>)-1,3-dimethyl-4(1′-phenylethylimino)piperidine

Authors

  • Г. B. Гришина M. V. Lomonosov Moscow State University, Moscow 119899
  • E. Л. Гайдарова M. V. Lomonosov Moscow State University, Moscow 119899
  • E. Р. Лукьяненко M. V. Lomonosov Moscow State University, Moscow 119899
  • А. А. Борисенко M. V. Lomonosov Moscow State University, Moscow 119899

Abstract

The stereochemistry of the asymmetric reduction of the imine obtained from 1,3-dimethylpiperidin-4-one and (S)-α-phenylethylamine has been studied. It is shown that hydride reduction of imine I by sodium borohydride in methanol is asymmetric and gives the cis and trans diastereomeric pair 1,3-dimethyl-4-(α-phenylethylamino)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-(α-phenylethylamino)piperidine which had been separated by column chromatography.

How to Cite
Grishina, G. V.; Gaidarova, E. L.; Luk'yanenko, E. R.; Borisenko, A. A. Chem. Heterocycl. Compd. 1996, 32, 194. [Khim. Geterotsikl. Soedin. 1996, 219.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01165445

 

Downloads

Published

1996-02-25

Issue

No. 2 (1996)

Section

Original Papers