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Preparations of deuterium labelled guvacine and isoguvacine
Author(s) -
Christensen Søren Brøgger,
KrogsgaardLarsen Povl
Publication year - 1980
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580170206
Subject(s) - chemistry , hydrobromide , triethylamine , thionyl chloride , hydrochloride , hydrolysis , demethylation , hydrogen–deuterium exchange , iodide , medicinal chemistry , organic chemistry , chloride , hydrogen , biochemistry , gene expression , dna methylation , gene
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.