A Low-Waste Process To Sertraline By Diastereomeric Crystal Resolution and Waste Isomer Racemisation

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Blacker, A. John, Brown, Stuart, Clique, Blandine, Gourlay, Brian, Headley, Catherine E., Ingham, Stephen, Ritson, Dougal, Screen, Thomas, Stirling, Matthew J., Taylor, David and Thompson, Gary (2009) A Low-Waste Process To Sertraline By Diastereomeric Crystal Resolution and Waste Isomer Racemisation. Organic Process Research and Development, 13 (6). pp. 1370-1378. ISSN 1083-6160

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Official URL: http://dx.doi.org/10.1021/op900112f

DOI: 10.1021/op900112f

Abstract

A semi-continuous method for recovering waste sertraline isomers from a diastereomeric crystallisation process is described in which the mother liquors from a highly selective mandelic acid resolution for the (1S,4S) isomer are treated sequentially with SCRAM, an iridium-based chiral amine racemisation catalyst, and then catalytic potassium tertiary butoxide to epimerise the methine chiral centre. The green, low-waste process also deals with recovery and recycle of the precious-metal catalyst, providing both good economics and high-quality product.

Item Type:	Article
Subjects:	Q Science > QD Chemistry
Schools:	School of Applied Sciences
Depositing User:	Graham Stone
Date Deposited:	12 Oct 2012 13:18
Last Modified:	12 Oct 2012 13:18
URI:	http://eprints.hud.ac.uk/id/eprint/15562

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