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Isolation and structural determination of non-racemic tertiary cathinone derivatives

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Isolation and structural determination of non-racemic tertiary cathinone derivatives. / Zhou, MengJie; Bouazzaoui, Samira; Jones, Louise E. et al.
In: Organic and Biomolecular Chemistry , Vol. 13, No. 37, 07.10.2015, p. 9629-9636.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Zhou, M, Bouazzaoui, S, Jones, LE, Goodrich, P, Bell, SJE, Sheldrake, GN, Horton, PN, Coles, SJ & Fletcher, N 2015, 'Isolation and structural determination of non-racemic tertiary cathinone derivatives', Organic and Biomolecular Chemistry , vol. 13, no. 37, pp. 9629-9636. https://doi.org/10.1039/C5OB01306B

APA

Zhou, M., Bouazzaoui, S., Jones, L. E., Goodrich, P., Bell, S. J. E., Sheldrake, G. N., Horton, P. N., Coles, S. J., & Fletcher, N. (2015). Isolation and structural determination of non-racemic tertiary cathinone derivatives. Organic and Biomolecular Chemistry , 13(37), 9629-9636. https://doi.org/10.1039/C5OB01306B

Vancouver

Zhou M, Bouazzaoui S, Jones LE, Goodrich P, Bell SJE, Sheldrake GN et al. Isolation and structural determination of non-racemic tertiary cathinone derivatives. Organic and Biomolecular Chemistry . 2015 Oct 7;13(37):9629-9636. Epub 2015 Aug 6. doi: 10.1039/C5OB01306B

Author

Zhou, MengJie ; Bouazzaoui, Samira ; Jones, Louise E. et al. / Isolation and structural determination of non-racemic tertiary cathinone derivatives. In: Organic and Biomolecular Chemistry . 2015 ; Vol. 13, No. 37. pp. 9629-9636.

Bibtex

@article{a023ee1713cc4a15b811c05c85010175,
title = "Isolation and structural determination of non-racemic tertiary cathinone derivatives",
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. ",
author = "MengJie Zhou and Samira Bouazzaoui and Jones, {Louise E.} and Peter Goodrich and Bell, {Steven J.E.} and Sheldrake, {Gary N.} and Horton, {Peter N.} and Coles, {Simon J.} and Nick Fletcher",
note = "pdf visibility currently marked backend. PC taking to Roadmap to clarify who has permission to make exemptions to the usual policy. ",
year = "2015",
month = oct,
day = "7",
doi = "10.1039/C5OB01306B",
language = "English",
volume = "13",
pages = "9629--9636",
journal = "Organic and Biomolecular Chemistry ",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "37",

}

RIS

TY - JOUR

T1 - Isolation and structural determination of non-racemic tertiary cathinone derivatives

AU - Zhou, MengJie

AU - Bouazzaoui, Samira

AU - Jones, Louise E.

AU - Goodrich, Peter

AU - Bell, Steven J.E.

AU - Sheldrake, Gary N.

AU - Horton, Peter N.

AU - Coles, Simon J.

AU - Fletcher, Nick

N1 - pdf visibility currently marked backend. PC taking to Roadmap to clarify who has permission to make exemptions to the usual policy.

PY - 2015/10/7

Y1 - 2015/10/7

N2 - 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.

AB - 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.

U2 - 10.1039/C5OB01306B

DO - 10.1039/C5OB01306B

M3 - Journal article

VL - 13

SP - 9629

EP - 9636

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 37

ER -