Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1795–1807 | Cite as

N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines

  • D. A. GruzdevEmail author
  • S. A. Vakarov
  • G. L. Levit
  • V. P. Krasnov

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.


amines (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine N-tosyl-(S)-proline acylation diastereoisomers kinetic resolution stereoselectivity 


The work was performed with financial support from the Russian Foundation for Basic Research (grants 12-03-31615, 12-03-33029, 13-03-00674), the Ural Branch of the Russian Academy of Sciences (project 12-P-3-1030), and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).

The authors are grateful to L. Sh. Sadretdinova for performing the HPLC analyses, and to Cand. Chem. Sci. M. I. Kodess for the recording of NMR spectra.


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • D. A. Gruzdev
    • 1
    Email author
  • S. A. Vakarov
    • 1
  • G. L. Levit
    • 1
  • V. P. Krasnov
    • 1
  1. 1.I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of SciencesYekaterinburgRussia

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