Synthesis and resolution of nicotine
AssigneeNjoy, LLC
InventorsBert Willis, Mohammed Moinuddin Ahmed, Wesley Freund, Douglas Sawyer
Life of this patent
Estimating the term…
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).
Claims9
A method of preparing a nicotine composition, the method comprising:
- separating a salt from a solution comprising (−)—O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA), (S)—(−)-nicotine, and (R)—(−)-nicotine, wherein the salt comprises (S)—(−)-nicotine and L-PTTA;
- and
- separating (S)—(−)-nicotine from the salt;
- wherein the nicotine composition has an enantiomeric excess of (S)—(−)-nicotine ranging from about 40% to 100%.
Dependencies are inferred from the claim text.