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Issue 37, 2015
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Isolation and structural determination of non-racemic tertiary cathinone derivatives

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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.

Graphical abstract: Isolation and structural determination of non-racemic tertiary cathinone derivatives

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Publication details

The article was received on 26 Jun 2015, accepted on 05 Aug 2015 and first published on 06 Aug 2015


Article type: Paper
DOI: 10.1039/C5OB01306B
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 9629-9636
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    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 and N. C. Fletcher, Org. Biomol. Chem., 2015, 13, 9629
    DOI: 10.1039/C5OB01306B

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