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

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.

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