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Synthesis of (±)-[1,1′-15N2, 2′-13C]-trans-3′-methylnicotine

✍ Scribed by Sarath R. Sirimanne; Vincent L. Maggio; Donald G. Patterson Jr.

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
445 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of (±)‐[1,1′‐^15^N~2~, 2′‐^13^C]‐trans‐3′‐methylnicotine is reported. ^15^N‐3‐Bromopyridine obtained from bromination of pyridine was formulated with nBuLi/[carbonyl‐^13^C]‐methyl formate. The resulting ^15^N‐Pyridine‐3‐[^13^C‐carbonyl]‐carboxaldehyde was reacted with ^15^N‐methylamine and then the resulting Schiff's base was condensed with succinic anhydride to give (±)‐[1,1′‐^15^N~2~, 5′‐^13^C]‐trans‐4′‐carboxycotinine. Reduction with lithium aluminium hydride and mesylation followed by reduction with Zn/Nal gave (±)‐[1,1′‐^15^N~2~, 2′‐^13^C]‐trans‐3′‐methylnicotine.

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