Preparation method for synthesizing chiral nicotine from chiral tert-butyl sulfinamide

Abstract

The invention discloses a preparation method for synthesizing chiral nicotine from chiral tert-butyl sulfinamide. The preparation method comprises the following steps: carrying out a condensation reaction on 3-pyridylaldehyde and chiral tert-butyl sulfinamide under the action of titanate; then carrying out a reaction on a condensation product and (1,3-dioxan-2-ylethyl)magnesium bromide; performing cyclization under an acidic condition; and finally, carrying out reduction and aminomethylation to obtain the chiral nicotine. The novel synthesis method of chiral nicotine provided by the invention has the advantages that a reaction route is short, raw materials are easy to obtain and low in price since chiral tert-butyl sulfinamide is taken as a starting raw material, expensive or complex chiral catalysts do not need to be prepared, each step of reaction operation is simple, and the chiral nicotine generated by the reaction is high in yield, high in ee value and reduced in production cost.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method for synthesizing chiral nicotine from chiral tert-butylsulfinamide. Background technique [0002] With the rapid development of the electronic cigarette industry, nicotine, as one of the important active ingredients of electronic cigarettes, is in increasing demand, and nicotine in a single configuration with optical activity has attracted widespread attention. However, there are few studies on the preparation methods of chiral nicotine at present, and they are basically obtained by chiral resolution, but chiral resolution reagents are expensive, which is not conducive to industrial production. [0003] The patent with the publication number CN104341390A discloses a preparation method of chiral nicotine, which uses a cyclic imine as a starting material and requires an expensive chiral catalyst, and uses a chiral catalyst to induce the formation of ...

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Problems solved by technology

The patent with publication number CN11233829A discloses a preparation method of optically active nicotine, using nitrogen-containing or phosphorus-containing chiral ligands to prepare organometallic catalysts, and preparing chiral nicotine with imide salt derivatives as starting materials. Similarly, an organometallic catalyst prepared with a nitrogen-containing or phosphorus-containing chiral ligand is used as a chiral catalyst to induce the formation of a chiral center. The preparation method of the organometallic catalyst is more complicated and the production cost is higher.

The applicant found that the use of chiral catalysts makes the whole synthesis of chiral nicotine more reaction steps, resulting in a lower yield of chiral nicotine

[0004] Chiral tert-butyl sulfinamide is a raw material with a wide range of sources and low price, but there is no report on the synthesis of chiral nicotine using chiral tert-butyl sulfinamide as a raw material

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