Home > Research > Publications & Outputs > Isolation and structural determination of non-r...

Associated organisational unit

Electronic data

  • OB-ART-06-2015-001306_Revised_Manu

    Accepted author manuscript, 2.2 MB, PDF document

    Available under license: CC BY-NC: Creative Commons Attribution-NonCommercial 4.0 International License

Links

Text available via DOI:

View graph of relations

Isolation and structural determination of non-racemic tertiary cathinone derivatives

Research output: Contribution to journalJournal article

Published
  • MengJie Zhou
  • Samira Bouazzaoui
  • Louise E. Jones
  • Peter Goodrich
  • Steven J.E. Bell
  • Gary N. Sheldrake
  • Peter N. Horton
  • Simon J. Coles
  • Nick Fletcher
Close
<mark>Journal publication date</mark>7/10/2015
<mark>Journal</mark>Organic and Biomolecular Chemistry
Issue number37
Volume13
Number of pages8
Pages (from-to)9629-9636
Publication statusPublished
Early online date6/08/15
Original languageEnglish

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.

Bibliographic note

pdf visibility currently marked backend. PC taking to Roadmap to clarify who has permission to make exemptions to the usual policy.