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Preparations of deuterium labelled guvacine and isoguvacine

✍ Scribed by Søren Brøgger Christensen; Povl Krogsgaard-Larsen

Publisher
John Wiley and Sons
Year
1980
Tongue
French
Weight
443 KB
Volume
17
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The preparations of guvacine hydrochloride, in which a proton in position 2 (11) and protons in positions 2 and 5 (10) are selectively exchanged by deuterium, and of [2,6‐^2^H]isoguvacine hydrobromide (14a) are described. The deuterium labelled guvacine salts 10 and 11 were synthesized by triethylamine catalyzed exchange of hydrogen for deuterium in methyl N‐nitroso‐1,2,5,6‐tetrahydropyridine‐3‐carboxylate (3) followed by denitrosation and hydrolysis. Treatment of N‐nitroso‐1,4,5,6‐tetrahydropyridine‐3‐carboxylic acid with methanolic thionyl chloride gave 3,4,5,6‐tetrahydropyridin‐3‐on ketoxime. Compound 14a was prepared by sodium borodeuteride reduction of 4‐ethoxycarbonyl‐1‐methylpyridinium iodide (12) followed by N‐demethylation and hydrolysis of the intermediate.

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