Isolation and structural determination of non-racemic tertiary cathinone derivatives

Zhou, MengJie and Bouazzaoui, Samira and Jones, Louise E. and Goodrich, Peter and Bell, Steven J.E. and Sheldrake, Gary N. and Horton, Peter N. and Coles, Simon J. and Fletcher, Nick (2015) Isolation and structural determination of non-racemic tertiary cathinone derivatives. Organic and Biomolecular Chemistry, 13 (37). pp. 9629-9636. ISSN 1477-0520

[img]
Preview
PDF (OB-ART-06-2015-001306_Revised_Manu)
OB_ART_06_2015_001306_Revised_Manu.pdf - Accepted Version
Available under License Creative Commons Attribution-NonCommercial.

Download (2MB)

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.

Item Type:
Journal Article
Journal or Publication Title:
Organic and Biomolecular Chemistry
Additional Information:
pdf visibility currently marked backend. PC taking to Roadmap to clarify who has permission to make exemptions to the usual policy.
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/aacsb/disciplinebasedresearch
Subjects:
ID Code:
75018
Deposited By:
Deposited On:
06 Aug 2015 10:00
Refereed?:
Yes
Published?:
Published
Last Modified:
26 Sep 2020 03:24