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Synthesis method of (S)-nicotine

A synthesis method and technology of nicotine, applied in the direction of organic chemistry, fermentation, etc., can solve the problems of non-recovery, no practical application value, high cost, etc.

Pending Publication Date: 2021-09-10
PORTON FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] However, the chiral auxiliary reagent method of this method requires the use of stoichiometric chiral auxiliary reagents, which cannot be recovered, resulting in high costs and no practical application value.
[0013] In summary, various (S)-nicotine chemical synthesis methods in the prior art have deficiencies, and more economical, effective and safe synthetic methods need to be developed

Method used

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  • Synthesis method of (S)-nicotine
  • Synthesis method of (S)-nicotine
  • Synthesis method of (S)-nicotine

Examples

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Embodiment 1

[0059] This example prepares the compound Mesmin, and its synthesis method is carried out with reference to the method in the patent document EP2487172A1, and the obtained product is characterized by proton nuclear magnetic spectrum, and the characterization diagram is as follows figure 1 As shown, the NMR data results are: 1 H-NMR (400MHz, CDCl 3 ): δppm 8.97(1H,d),8.64(1H,dd),8.17(1H,dt),7.29-7.34(m,1H),4.06(2H),2.91-2.96(m,2H),2.01-2.09 (m,2H). It indicated that mesmin was synthesized successfully. The sample is analyzed and detected by high-performance liquid chromatography, and its purity is 99.3%, and the chromatographic characterization diagram is as follows figure 2 shown.

Embodiment 2

[0061] This embodiment provides a synthetic method of (S)-nornicotine, the operation method is as follows:

[0062] Add 3 g of mesmin into a 50 mL three-neck round bottom flask, add 10 mL of 0.1 M phosphate buffer, and adjust the pH to 6.0. Then add 5.5 g of glucose into the reaction flask and stir until completely dissolved. In another 50mL flask, add 0.2g imine reductase IRED103, 0.04g glucose dehydrogenase GDH109 and 0.008g NADP salt, stir until completely dissolved. Then the solution in the second flask was slowly added to the first flask, the temperature was raised to 25°C, and the reaction was stirred at 300r / min for 24h. After filtration, the filtrate was extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated to obtain 2.2 g of (S)-nornicotine.

[0063] The prepared (S)-nornicotine is characterized by proton nuclear magnetic spectrum, and the characterization diagram is as follows image 3 As shown, the NMR data results are: 1 H-NMR (400MHz...

Embodiment 3

[0066] This embodiment provides a synthetic method of (S)-nornicotine, the operation method is as follows:

[0067] Add 3 g of mesmin to a 50 mL three-neck round bottom flask, add 15 mL of 0.1 M phosphate buffer, and adjust the pH to 5.8. Then add 5.5 g of glucose into the reaction flask and stir until completely dissolved. In another 50mL flask, add 0.3g imine reductase IRED103, 0.04g glucose dehydrogenase GDH102 and 0.01g NADP salt, stir until completely dissolved. Then slowly add the solution in the second flask to the first flask, raise the temperature to 37°C, and stir for 24h. After filtration, the filtrate was extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated to obtain 2.4 g of (S)-nornicotine.

[0068] Utilize high-performance liquid chromatography to carry out the mensuration of chemical purity and optical purity to the (S)-nornicotine that makes respectively, concrete operation method is the same as embodiment 2, and chromatogram is a...

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Abstract

The invention relates to a synthesis method of (S)-nicotine, which comprises the following steps of: under the condition of a coenzyme circulation system, taking coenzyme as a hydrogen donor, taking imine reductase as a catalyst, carrying out catalytic reduction on myosmine to obtain (S)-nornicotine, and carrying out methylation reaction on the (S)-nornicotine to obtain the (S)-nicotine. The synthesis method of the (S)-nicotine disclosed by the invention is simple to operate, safe, reliable, high in yield and low in cost, and has excellent chemical selectivity; the purity of the product can reach 99.5% or above; the (S)-nicotine also has excellent enantioselectivity; and the optical purity can reach 99.5% or above.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing (S)-nicotine, in particular to a method for synthesizing (S)-nicotine with high chemical purity and high optical purity. Background technique [0002] (S)-Nicotine (nicotine) is an alkaloid found in plants of the Solanaceae family (Solanum genus) and an important constituent of tobacco. Tobacco leaves contain 1.5%-3.5% (S)-nicotine. Extracting nicotine from tobacco leaves is currently the most important method to obtain nicotine. Although there have been related reports on chemical synthesis methods, the chemical synthesis methods are still immature. The cost is much higher than the extraction method. The chemical synthesis methods that have been reported so far include chemical resolution, asymmetric hydrogenation, and chiral auxiliary reagents. [0003] Patent US20160326134 reports the method of obtaining (S)-nicotine by using methyl nicoti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/16
CPCC12P17/165C07D401/04C12Y105/01
Inventor 林文清郑宏杰陈泽聪朱剑平乐庸堂胡集铖王建冲李凌宇刘小波
Owner PORTON FINE CHEM
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