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

Sarath R. Sirimanne, Vincent L. Maggio, Donald George Jr Patterson

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The synthesis of (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine is reported. 15N‐3‐Bromopyridine obtained from bromination of pyridine was formulated with nBuLi/[carbonyl‐13C]‐methyl formate. The resulting 15N‐Pyridine‐3‐[13C‐carbonyl]‐carboxaldehyde was reacted with 15N‐methylamine and then the resulting Schiff's base was condensed with succinic anhydride to give (±)‐[1,1′‐15N2, 5′‐13C]‐trans‐4′‐carboxycotinine. Reduction with lithium aluminium hydride and mesylation followed by reduction with Zn/Nal gave (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine.

Original languageEnglish (US)
Pages (from-to)163-174
Number of pages12
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume31
Issue number3
DOIs
StatePublished - Jan 1 1992

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Schiff Bases
Halogenation
pyridine
methyl formate
succinic anhydride
lithium aluminum hydride

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Sirimanne, Sarath R. ; Maggio, Vincent L. ; Patterson, Donald George Jr. / Synthesis of (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine. In: Journal of Labelled Compounds and Radiopharmaceuticals. 1992 ; Vol. 31, No. 3. pp. 163-174.
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Synthesis of (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine. / Sirimanne, Sarath R.; Maggio, Vincent L.; Patterson, Donald George Jr.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 31, No. 3, 01.01.1992, p. 163-174.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine

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N2 - The synthesis of (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine is reported. 15N‐3‐Bromopyridine obtained from bromination of pyridine was formulated with nBuLi/[carbonyl‐13C]‐methyl formate. The resulting 15N‐Pyridine‐3‐[13C‐carbonyl]‐carboxaldehyde was reacted with 15N‐methylamine and then the resulting Schiff's base was condensed with succinic anhydride to give (±)‐[1,1′‐15N2, 5′‐13C]‐trans‐4′‐carboxycotinine. Reduction with lithium aluminium hydride and mesylation followed by reduction with Zn/Nal gave (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine.

AB - The synthesis of (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine is reported. 15N‐3‐Bromopyridine obtained from bromination of pyridine was formulated with nBuLi/[carbonyl‐13C]‐methyl formate. The resulting 15N‐Pyridine‐3‐[13C‐carbonyl]‐carboxaldehyde was reacted with 15N‐methylamine and then the resulting Schiff's base was condensed with succinic anhydride to give (±)‐[1,1′‐15N2, 5′‐13C]‐trans‐4′‐carboxycotinine. Reduction with lithium aluminium hydride and mesylation followed by reduction with Zn/Nal gave (±)‐[1,1′‐15N2, 2′‐13C]‐trans‐3′‐methylnicotine.

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