Chemical studies on tobacco smoke XXIII. Synthesis of carbon-14 labelled myosmine, nornicotine and N′-nitrosonornicotine
✍ Scribed by M. W. Hu; W. E. Bondinell; D. Hoffmann
- Book ID
- 102369394
- Publisher
- John Wiley and Sons
- Year
- 1974
- Tongue
- French
- Weight
- 319 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
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.