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The synthesis of [14C]-3S,4R-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine hydrochloride (BRL 29060A), and mechanistic studies using carbon-13 labelling

✍ Scribed by K. Willcocks; R. D. Barnes; D. C. Rustidge; D. J. D. Tidy

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
555 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Paroxetine, BRL 29060A 1 has been labelled with both carbon‐14 and carbon‐13. Hydroxymethylation of 4‐(4‐fluorophenyl)‐1‐methyl‐1,2,5,6‐tetrahydropyridine, using [^14^C]formaldehyde, produced an enantiomeric mixture of products which was taken without separation through a multistage sequence. Resolution of the mixture of stereoisomers at the penultimate step gave [^14^C]BRL 29060A with the required configuration. The overall radiochemical yield was 8%. At some stage in this process, as shown by C‐13 labelling studies, scrambling of the label took place to give BRL 29060A with the majority of the label in the C‐2 position of the piperidine ring and the remainder at the expected 7‐methylene position. Further investigations of this route using carbon‐13 as the label are described. When sesamol, (3,4‐methylenedioxyphenol) was reacted with the O‐benzene sulphonate of (±)‐cis‐4‐(4‐fluorophenyl)‐3‐(hydroxy[^13^C]methyl)‐l‐methylpiperidine, an inversion of configuration resulted via the previously described 1‐aza[3.1.1]bicycloheptane ring system. It is also shown that the corresponding (±)‐trans‐substituted piperidine, under similar conditions, does not undergo this inversion.

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