Method for asymmetrically synthesizing (S)-nicotine

An asymmetric and nicotine technology, applied in organic chemical methods, bulk chemical production, organic chemistry, etc., to achieve the effects of lower prices, lower production costs, and mild reaction conditions
CN113979993APending Publication Date: 2022-01-28云南萃精生物科技有限责任公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
云南萃精生物科技有限责任公司
Publication Date
2022-01-28

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Abstract

The invention provides a method for asymmetrically synthesizing (S)-nicotine. The method comprises the following steps: condensing 3-pyridylaldehyde and (R)-tert-butanesulfinamide to obtain chiral imine; adding ethyl acetoacetate to react with the chiral imine to obtain chiral amine; removing tert-butyl sulfinyl and ester group from the chiral amine to obtain chiral aminoketone; protecting the amino group of the chiral aminoketone by using phthalic anhydride; adding a brominating agent to brominate the chiral aminoketone to obtain bromide; and adding hydrazine hydrate to remove a Pht protecting group and form a tetrahydropyrrole ring at the same time by utilizing a one-pot method, reducing carbonyl into methylene to obtain (S)-nornicotine, and carrying out N-methylation on the (S)-nornicotine to obtain the final product (S)-nicotine. According to the method, direct construction of chiral carbon is realized by utilizing a cheap chiral reagent (R)-tert-butanesulfinamide, (S)-nicotine with high chiral purity is obtained at a relatively high yield through subsequent simple reaction steps, and the method is simple, convenient, feasible and suitable for industrial production.
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Description

technical field

[0001] The invention relates to the technical field of chemical synthesis, in particular to a method for asymmetrically synthesizing (S)-nicotine. Background technique

[0002] Nicotine (the English name is Nicotine and the chemical name is 1-methyl-2-(3'-pyridine) pyrrolidine), also known as nicotine. Nicotine was first isolated from tobacco in 1825 by Swiss chemist Pequet. In 1893, Peer was the first to determine the chemical structure of nicotine completely by chemical method. In 1928, Spath and Bretschneider chemically synthesized nicotine and confirmed the chemical structure of nicotine again.

[0003] Nicotine is a key component of tobacco alkaloids and is widely used in tobacco-related products. At the same time, nicotine and its derivatives niacin, niacinamide, nicotinic acid ester, etc. have a variety of physiological activities, such as the treatment of depression, anxiety, and the treatment of Alzheimer's disease, Parkinson's syndrome, and anti-...

Claims

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