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Synfacts 2007(9): 0896-0896  
DOI: 10.1055/s-2007-968839
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Selective Estrogen Receptor β-Modulator

Contributor(s): Philip Kocienski
M. A. Huffman*, J. D. Rosen, R. N. Farr, J. E. Lynch
Merck & Co., Inc., Rahway, USA
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

The target molecule (I) is being developed to avoid the adverse side effects of hormone replacement therapy. The key step is an asymmetric phase-transfer-catalyzed alkylation of the indanone D using commercial N-(p-trifluoro­methylbenzyl)cinchoninium bromide (E) as catalyst. For a related indanone alkylation, see: A. Bhattacharya et al. Angew. Chem., Int. Ed. Engl. 1986, 25, 476.