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Synfacts 2007(1): 0008-0008  
DOI: 10.1055/s-2006-955657
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of DOV21947

Contributor(s): Philip Kocienski
F. Xu*, J. A. Murry, B. Simmons, E. Corley, K. Fitch, S. Karady, D. Tschaen
Merck Research Laboratories, Rahway, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

DOV21947 is in clinical trials for the treatment of pain. It is a potent inhibitor of serotonin and norepinephrine reuptake transporters and it is an N-methyl-d-aspartate agonist. The Merck paper describes a careful optimization study of two key steps: (a) the selective alkylation of (S)-(+)-epi­chlorohydrin at C3 leading to A and (b) the selective cyclization of the metallated ketimine via rotamer D.