Synthesis and resolution of nicotine
AssigneeNjoy, LLC
InventorsBert Willis, Mohammed Moinuddin Ahmed, Wesley Freund, Douglas Sawyer
Life of this patent
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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).
Claims17
A method of preparing (S)-(−)-nicotine or a salt thereof, the method comprising:
- combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof;
- reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or a salt thereof;
- enriching (S)-(−)-nicotine by combining the racemic nicotine with (−)-O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA) to produce a nicotine-L-PTTA salt;
- and
- isolating the (S)-(−)-nicotine from the nicotine-L-PTTA salt.
A method of preparing (S)(−)-nicotine or a salt thereof, the method comprising:
- reducing 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or salt thereof;
- resolving the racemic nicotine by combining the racemic nicotine with (−)-O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA) to produce a nicotine-L-PTTA salt;
- and
- separating (S)(−)-nicotine from the nicotine-L-PTTA salt.
Dependencies are inferred from the claim text.