SYNTHESIS OF ENANTIOMERS OF 6-NITRO- AND 6-AMINO-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINES

Authors

  • Д. А. Груздев I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Г. Л. Левит I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • М. И. Кодесс I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • В. П. Краснов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1194

Keywords:

amides, diastereoisomers, enantiomers, kinetic resolution, nitration, reduction

Abstract

Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the diastereoisomeric amides and acidic hydrolysis. The introduction of a trifluoroacetyl protecting group into the position 1 of the enantio pure nitro compound followed by the reduction led to (S)-6-amino-2-methyl-1-trifluoroacetyl-1,2,3,4-tetra-hydroquinoline in a high yield.

Authors: D. A. Gruzdev, G. L. Levit, M. I. Kodess, and V. P. Krasnov.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (5), pp 748-757

http://link.springer.com/article/10.1007/s10593-012-1053-8

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Published

2013-11-20

Issue

No. 5 (2012)

Section

Original Papers