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Synlett 2010(5): 753-756  
DOI: 10.1055/s-0029-1219383
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple Route Toward New Clomiphene Metabolites

Bruno C. Vitorianoa, Luísa C. R. Carvalhoa, Mónica S. Estevãoa, Michael H. Sekerab, M. Manuel B. Marques*a
a REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal
Fax: +351(21)2948550; e-Mail: mmbmarques@dq.fct.unl.pt;
b Laboratório de Análises de Dopagem, Autoridade Antidopagem de Portugal, Av. Prof. Egas Moniz (Estádio Universitário),1600-190 Lisboa, Portugal
Further Information

Publication History

Received 25 November 2009
Publication Date:
10 February 2010 (online)

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Abstract

A new clomiphene metabolite, extremely useful for doping analysis, was synthesized in 19% overall yield. The approach involved a Grignard reaction via a N-acylbenzotriazole intermediate to afford a key aromatic ketone and a HWE reaction. Both stereo­isomers were separated and identified.

Key words

clomiphene - Grignard reactions - N-acylbenzotriazole - olefination - drugs

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