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Chemistry of Heterocyclic Compounds

, Volume 32, Issue 2, pp 194–196 | Cite as

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

  • G. V. Grishina
  • E. L. Gaidarova
  • E. R. Luk'yanenko
  • A. A. Borisenko
Article
  • 26 Downloads

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 1 by sodium borohydride in methanol is asymmetric and gives the cis and trans diastereomeric pair 1,3-dimethyl-4-(α-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-(α-phenylethylamino)piperidine which had been separated by column chromatography.

Keywords

Sodium Methanol Chromatography Organic Chemistry Hydride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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    W. F. M. van Bever, C. J. E. Niemegeers, and P. A. J. Janssen, J. Med. Chem.,17, 1047 (1974).Google Scholar
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    G. V. Grishina and E. L. Gaidarova, Khim. Geterotsikl. Soedin., No. 8, 1072 (1992).Google Scholar

Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • G. V. Grishina
    • 1
  • E. L. Gaidarova
    • 1
  • E. R. Luk'yanenko
    • 1
  • A. A. Borisenko
    • 1
  1. 1.M. V. Lomonosov State UniversityMoscow

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