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Synlett 2007(8): 1211-1214  
DOI: 10.1055/s-2007-977414
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Efficient New Synthesis of Racemic Cetiedil and a Novel Route to α-Ketocarboxylic Acids Utilising Mild Conditions

Craig J. Roxburgh*, C. Robin Ganellin, Andrew J. Thorpe
Department of Chemistry, Christopher Ingold Laboratories, University College London, London, WC1H OAJ, UK
e-Mail: sic@inm.mod.uk;
Further Information

Publication History

Received 25 November 2006
Publication Date:
03 April 2007 (online)

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Abstract

We describe a new efficient synthesis of the prescribed racemic drug cetiedil [(±)-2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1H-azepin-1-yl)ethylester]. Additionally, we report herein a high yielding large scale, route to its acid precursor 7, subsequently enabling large-scale synthesis of the chiral forms of cetiedil, and detailed pharmacological investigations.

Additionally, we describe a novel route to α-ketocarboxylic acids, starting from readily available or easily obtainable aldehydes: The mild conditions utilised opens up its applicability for use on molecules of biological interest.

Key words

cetiedil - enantiomers - synthesis - α-ketocarboxylic ­acids - Swern oxidation

1

Current address: The Institute of Naval Medicine, Alverstoke, Gosport, Hants, PO12 2DL, UK.