Premium
Synthesis of (±)‐[1,1′‐ 15 N 2 , 2′‐ 13 C]‐ trans ‐3′‐methylnicotine
Author(s) -
Sirimanne Sarath R.,
Maggio Vincent L.,
Patterson Donald G.
Publication year - 1992
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.2580310302
Subject(s) - chemistry , pyridine , methylamine , medicinal chemistry , lithium aluminium hydride , lithium (medication) , succinic anhydride , formate , halogenation , organic chemistry , polymer chemistry , catalysis , medicine , endocrinology
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.