Chemical studies on tobacco smoke XXIII. Synthesis of carbon‐14 labelled myosmine, nornicotine and N′‐nitrosonornicotine
- 1 January 1974
- journal article
- research article
- Published by Wiley in Journal of Labelled Compounds and Radiopharmaceuticals
- Vol. 10 (1) , 79-88
- https://doi.org/10.1002/jlcr.2590100110
Abstract
Dl‐Nornicotine‐2′‐14C was synthesized in four steps. Nicotinic acid (carboxyl‐14C) was first esterified with diazomethane to yield methyl nicotinate (carboxyl‐14C). The ester was condensed with 3‐lithio‐N‐trimethylsilyl‐2‐pyrrolidone to give 3‐nicotinoyl‐N‐trimethyslsilyl‐2‐pyrrolidone (ketone carbonyl‐14C), which was hydrolyzed and decarboxylated in concentrated hydrochloric acid to give myosmine‐2′‐14C.Reduction of myosmine‐2′14C gave nornicotine‐2′‐14C. Reaction of nornicotine‐2′‐14C in hydrochloric acid with sodium nitrite gave N′‐nitrosonornicotine‐2′‐14C. Purification of labelled myosmine, nornicotine, and N′‐nitrosonornicotine was accomplished by preparative thin layer chromatography.Keywords
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