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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

Pending Publication Date: 2022-01-28
云南萃精生物科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a kind of method of asymmetric synthesis (S)-nicotine, to solve the problem of existing route in the above-mentioned background technology

Method used

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  • Method for asymmetrically synthesizing (S)-nicotine
  • Method for asymmetrically synthesizing (S)-nicotine
  • Method for asymmetrically synthesizing (S)-nicotine

Examples

Experimental program
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Embodiment 1

[0035] A synthetic method for optically pure (S)-nicotine, the steps are as follows:

[0036] (1) Dissolve 3-pyridinecarbaldehyde (0.5mol) in ethanol (200mL), add (R)-tert-butylsulfinamide (0.55mol) and 0.60mol potassium hydrogensulfate, stir at room temperature for 3h, and depressurize Concentrate to remove ethanol, add 50mL water to the concentrated solution, and extract twice with ethyl acetate (150mL each time), combine the extracts and sequentially wash with dilute hydrochloric acid (0.1mol / L, 10mL dosage), water (25mL) and saturated salt Wash with water (15 mL), dry over anhydrous sodium sulfate (50 g), evaporate the solvent under reduced pressure, and obtain the product chiral imine;

[0037] (2) Under the ice bath, the chiral imine (0.1mol) obtained in the previous step was added to the ethanol (25mL) solution of the mixture of 0.1mol ethyl acetoacetate and 0.12mol sodium ethoxide, and the stirring reaction was continued under the ice bath until Thin-layer chromatogra...

Embodiment 2

[0044] A synthetic method for optically pure (S)-nicotine, the steps are as follows:

[0045] (1) Dissolve 3-pyridinecarbaldehyde (0.2mol) in ethanol (60mL), add 0.22mol of (R)-tert-butylsulfinamide and 38g of copper sulfate (0.24mol), stir at room temperature for 6h, and concentrate under reduced pressure 15mL of water was added to the concentrated solution, and extracted twice with ethyl acetate (25mL each time), the combined extracts were washed with dilute hydrochloric acid (0.1mol / L, 5mL), water (20mL) and saturated brine (10mL) successively , dried over anhydrous sodium sulfate (40 g). The solvent is evaporated under reduced pressure to obtain the product chiral imine, which can be directly used in the next reaction;

[0046] (2) Under ice bath, add the chiral imine (0.1mol) obtained in the previous step to the ethanol (50mL) solution of the mixture of 0.1mol ethyl acetoacetate and 0.12mol potassium tert-butoxide, and continue to stir under ice bath React until the thi...

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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.

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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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04C07B2200/07Y02P20/55
Inventor 杨蕾
Owner 云南萃精生物科技有限责任公司
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