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Synthesis of 14C-labeled piperidines and application to synthesis of [14C]SCH 351125, a CCR5 receptor antagonist

✍ Scribed by Sumei Ren; Paul McNamara; Pernilla Royster; Jae Lee; Surinderjit S. Saluja; David Koharski; Sharon Hendershot; Van Truong

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
115 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

1‐Benzyl‐4‐hydroxy[2‐^14^C]piperidine, a useful intermediate in labeled compound synthesis, was prepared from [^14^C]formaldehyde in high yield. The distribution pattern of ^14^C 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. [^14^C]SCH 351125, required for metabolism studies, was prepared from 1‐benzyl‐4‐hydroxy[2‐^14^C]piperidine in six steps. [^14^C]SCH 351125 is a mixture of four atropisomers. Preparation of [^14^C]SCH 351125 besylate salt of the desired atropisomer pair is also described. Copyright © 2007 John Wiley & Sons, Ltd.

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