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Convenient syntheses of N‐CD 3 labelled nicotine and nicotine analogues
Author(s) -
Seeman Jeffrey I.,
Secor Henry V.,
Forrest Gary
Publication year - 1979
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.2580160304
Subject(s) - chemistry , nicotine , iminium , sodium cyanoborohydride , alkylation , amide , amine gas treating , imine , lithium (medication) , salt (chemistry) , medicinal chemistry , alkyl , alkaloid , organic chemistry , stereochemistry , ion , medicine , neuroscience , biology , endocrinology , catalysis
Two procedures for the preparation of N‐CD 3 labelled nicotine and nicotine analogues are reported. These include: (a) the deuteroiodomethylation of the lithium amide of the corresponding secondary amine; and (b) the alkylation of the corresponding cyclic imine followed by sodium cyanoborohydride reduction of the resulting alkyl iminium salt. Products having both high chemical and isotopic purity are formed.