Isolation and structural determination of non-racemic tertiary cathinone derivatives

M. J. Zhou, S. Bouazzaoui, L. E. Jones, P. Goodrich, S. E J Bell, G. N. Sheldrake, P. N. Horton, S. J. Coles, N. C. Fletcher*

*Corresponding author for this work

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The racemic tertiary cathinones N,N-dimethylcathinone (1), N,N-diethylcathinone (2) and 2-(1-pyrrolidinyl)-propiophenone (3) have been prepared in reasonable yield and characterized using NMR and mass spectroscopy. HPLC indicates that these compounds are isolated as the anticipated racemic mixture. These can then be co-crystallized with (+)-O,O′-di-p-toluoyl-d-tartaric, (+)-O,O′-dibenzoyl-d-tartaric and (-)-O,O′-dibenzoyl-l-tartaric acids giving the single enantiomers S and R respectively of 1, 2 and 3, in the presence of sodium hydroxide through a dynamic kinetic resolution. X-ray structural determination confirmed the enantioselectivity. The free amines could be obtained following basification and extraction. In methanol these are reasonably stable for the period of several hours, and their identity was confirmed by HPLC and CD spectroscopy.

Original languageEnglish
Pages (from-to)9629-9636
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number37
Early online date06 Aug 2015
DOIs
Publication statusPublished - 07 Oct 2015

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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