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US 12,497,380 B2Granted
Method of asymmetrically synthesizing nicotine
OwnerShuang Gao, Qiwei Lang +1inventors
InventorsShuang Gao, Qiwei Lang, Xiaobing Ding
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Abstract
A method for preparing nicotine. (1) The nicotinic acid alkyl ester and N-methylpyrrolidone are subjected to a condensation reaction, and then added with a strong acid to obtain 4-methylamino-1-(3-pyridine)-butanone hydrochloride. (2) The 4-methylamino-1-(3-pyridine)-butanone hydrochloride is reacted with an amino-protecting reagent to obtain an intermediate (4). (3) A chiral alcohol (5) is obtained through an asymmetric reduction. (4) The chiral alcohol (5) is converted into the nicotine through a two-step reaction.
Claims5
A method for preparing formula (5), comprising:
- subjecting compound (4) to asymmetric reduction in the presence of a catalyst to produce the intermediate (5), as shown in the following reaction scheme:
- wherein R2 is selected from the group consisting of C1-2 alkyl, heteroatom-substituted alkyl, aryl and amino-protecting group;
- the catalyst is prepared through complexation of a metal salt with a chiral ligand;
- the metal salt is an inorganic salt of a transition element selected from the group consisting of iridium;
- and the chiral ligand is L3:
- the asymmetric reduction is performed in the presence of a base;
- and the base is potassium carbonate.
4 more elements
Dependencies are inferred from the claim text.