Synthesis and resolution of nicotine

US9809567B2 · kind B2 · utility

Assignee

• NJOY, LLC · US

Inventors

• Bert Willis · Mills River, US
• Mohammed Moinuddin Ahmed · Brevard, US
• Wesley A. Freund · Simpsonville, US
• Douglas B. Sawyer · Brookline, US

Key dates

• Filing date: Dec 8, 2015
• Grant date: Nov 7, 2017
• Expiry date: Dec 8, 2035

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D213/803
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present disclosure generally relates to methods of preparing nicotine and resolving R,S nicotine to enrich the (S)(−) enantiomer. The method may comprise combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a strong base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof; and reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or salt thereof. Resolving the racemic nicotine (or other enantiomeric mixture) may comprise combining the nicotine with (−)-O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA).