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Chemical studies on tobacco smoke XXIII. Synthesis of carbon‐14 labelled myosmine, nornicotine and N ′‐nitrosonornicotine
Author(s) -
Hu M. W.,
Bondinell W. E.,
Hoffmann D.
Publication year - 1974
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590100110
Subject(s) - nornicotine , chemistry , hydrochloric acid , diazomethane , hydrolysis , organic chemistry , chromatography , alkaloid
dl‐Nornicotine‐2′‐ 14 C was synthesized in four steps. Nicotinic acid (carboxyl‐ 14 C) was first esterified with diazomethane to yield methyl nicotinate (carboxyl‐ 14 C). The ester was condensed with 3‐lithio‐ N ‐trimethylsilyl‐2‐pyrrolidone to give 3‐nicotinoyl‐ N ‐trimethyslsilyl‐2‐pyrrolidone (ketone carbonyl‐ 14 C), which was hydrolyzed and decarboxylated in concentrated hydrochloric acid to give myosmine‐2′‐ 14 C. Reduction of myosmine‐2′ 14 C gave nornicotine‐2′‐ 14 C. Reaction of nornicotine‐2′‐ 14 C in hydrochloric acid with sodium nitrite gave N ′‐nitrosonornicotine‐2′‐ 14 C. Purification of labelled myosmine, nornicotine, and N ′‐nitrosonornicotine was accomplished by preparative thin layer chromatography.