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Synthesis of 14C‐labeled piperidines and application to synthesis of [14C]SCH 351125, a CCR5 receptor antagonist
Authors:Sumei Ren  Paul McNamara  Pernilla Royster  Jae Lee  Surinderjit S Saluja  David Koharski  Sharon Hendershot  Van Truong
Institution:Schering–Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA
Abstract:1‐Benzyl‐4‐hydroxy2‐14C]piperidine, a useful intermediate in labeled compound synthesis, was prepared from 14C]formaldehyde in high yield. The distribution pattern of 14C in the product is consistent with a mechanism involving reversible iminium ion formation and rapid equilibration of the iminium ion through a cationic aza‐Cope rearrangement. These steps precede the rate‐determining intramolecular cyclization step. SCH 351125 is a potent, selective CCR5 receptor antagonist with potential as a treatment for HIV infection. 14C]SCH 351125, required for metabolism studies, was prepared from 1‐benzyl‐4‐hydroxy2‐14C]piperidine in six steps. 14C]SCH 351125 is a mixture of four atropisomers. Preparation of 14C]SCH 351125 besylate salt of the desired atropisomer pair is also described. Copyright © 2007 John Wiley & Sons, Ltd.
Keywords:atropisomer  carbon‐14  CCR5  isotopic labeling  piperidine  HIV
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