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

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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.

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Journal Article
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Organic and Biomolecular Chemistry
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?? biochemistryorganic chemistryphysical and theoretical chemistrydiscipline-based research ??
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06 Aug 2015 10:00
Last Modified:
15 Jul 2024 15:21