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Synthesis process of nicotine with single configuration

A synthesis process and configuration technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, organic chemistry, etc., can solve the problem of high synthesis cost, achieve short reaction time and high e.e value , the effect of simple operation

Pending Publication Date: 2022-07-05
DALIAN TRICO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This process requires high-pressure reaction while using expensive noble metal salts such as ruthenium, rhodium, iridium, palladium, etc., and its synthesis cost is relatively high

Method used

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  • Synthesis process of nicotine with single configuration
  • Synthesis process of nicotine with single configuration
  • Synthesis process of nicotine with single configuration

Examples

Experimental program
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Effect test

preparation example

[0037] The preparation method of mesmin is described below by taking the preparation example 1 of mesmin as an example.

[0038] Preparation example 1 of mesmin provides a kind of preparation method of mesmin, and its synthetic route is as follows:

[0039] The specific preparation steps are:

[0040] Under nitrogen protection, 24.6 g of nicotinic acid was added to the reactor, and then 24.1 g of thionyl chloride was added dropwise for 1-2 hours. After the dropwise addition was completed, the temperature of the reaction system was increased to 70 °C, and the reaction was kept for 2 hours. , the excess thionyl chloride was removed under reduced pressure, and then the temperature was lowered to 25 ° C to obtain 28.2 g of nicotinyl chloride;

[0041] Add 150 g of trimethylbenzene, 18.5 g of pyrrolidone and 22.4 g of triethylamine to the four-necked flask, and then add 28.2 g of nicotinyl chloride dropwise. The reaction was carried out for 6h, then the temperature was lowered to...

Embodiment 1

[0050] The specific preparation steps are:

[0051] Under nitrogen protection, CuF (PPh) was added to the reactor 3 ) 32.0g of solid 2MeOH, 1g of L11 ligand, 250g of tetrahydrofuran, stirred at 25°C for 0.5h, added 20ml of PMHS liquid, and stirred at 25°C for 0.5h until the system turned dark red, then cooled the system to -10°C, Subsequently, 50 g of 50wt% maxmin tetrahydrofuran solution (maxmin and tetrahydrofuran solution 1:1) was added dropwise, the dropping time was 0.5h, and the dripping was completed at -10°C and stirred until the system turned yellow. At this time, maxmin reacted completely. ;

[0052] After the reaction of maxmin was completed, 1.5mol / mol of NH was added 4 F solution 200ml, stir for 1.0h to hydrolyze excess PMHS, and the hydrolysis reaction generates silyl ether;

[0053] The copper salt in the solution was removed by filtration under reduced pressure with 15 g silica gel, and the filter cake was washed with dichloromethane (2×10 mL DCM). The filt...

Embodiment 2

[0058] The specific preparation steps are:

[0059] Under nitrogen protection, CuF (PPh) was added to the reactor 3 ) 3 2.0g of 2MeOH solid, 1g of L12 ligand, and 250g of toluene, stirred at 25°C for 0.5h at a rotating speed, added 20ml of PMHS liquid, and stirred at 25°C for 0.5h until the system turned dark red, then cooled the system to 0°C, Subsequently, 50g of 50wt% maxesmin tetrahydrofuran solution (1:1 of maxmin and tetrahydrofuran solution) was added dropwise, and the dropping time was 0.5h.

[0060] After the reaction of maxmin was completed, 1.5mol / mol of NH was added 4 F solution 200ml, stir for 1.0h to hydrolyze excess PMHS, and the hydrolysis reaction generates silyl ether;

[0061] The copper salt in the solution was removed by filtration under reduced pressure with 15 g silica gel, and the filter cake was washed with dichloromethane (2×10 mL DCM). The filtrate was separated into phases, and the aqueous phase was extracted with dichloromethane (3×100 mL), and ...

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Abstract

The invention discloses a synthesis process of nicotine with a single configuration, which comprises the following steps: under the protection of nitrogen, taking myosmin as a substrate, and selectively reducing the myosmin in an organic solvent by using a copper salt-chiral organic ligand-hydrogen source catalytic system for the first time to obtain the nicotine with the single configuration. The single-configuration nornicotine is subjected to an aminomethylation reaction to obtain single-configuration nicotine. According to the synthesis process of the single-configuration nicotine, disclosed by the invention, the reaction time is shortened, the high-optical-purity single-configuration nornicotine is obtained through the asymmetric catalytic reduction reaction, the high-optical-purity nicotine is further obtained, and the total synthesis yield is improved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis process of single-configuration nicotine. Background technique [0002] Nicotine, also known as nicotine, is the most abundant alkaloid present in tobacco leaves. In the 1990s, "nicotine replacement therapy" was vigorously promoted around the world to help people get rid of tobacco dependence physically and psychologically. Nicotine is divided into R-type and S-type, of which S-type nicotine has high biological activity and R-type nicotine has poor activity. At present, nicotine is mainly extracted and purified from plants such as tobacco. The nicotine content obtained by this method is relatively low, and the cost remains high. [0003] In February 2021, Li Jiaquan's group patent CN112409327A announced a method for preparing nicotine with high optical purity, which utilizes biological enzyme-catalyzed asymmetric reduction technology. Using nicotinic acid...

Claims

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Application Information

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IPC IPC(8): C07D401/04B01J31/24
CPCC07D401/04B01J31/2452B01J31/2409C07B2200/07B01J2531/16
Inventor 王崇年刘长波杨志勇赵国荣王越江志强
Owner DALIAN TRICO CHEM
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