Synthesis method of 13-methyl berberine alkaloid

A technology of methyl berberine and a synthetic method, applied in directions such as organic chemistry, can solve the problems of complicated synthesis steps, complicated operation, high price and the like, and achieve the effects of simplified synthesis steps, easy operation and low cost

Active Publication Date: 2022-02-18
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above method has the following defects: 1. The synthesis steps are relatively cumbersome and the operation is complicated; 2. In order to better improve the conversion rate, the preparation requires a variety of expensive metal catalysts and excessive acid catalysis, so the production capacity is low and the price is expensive

Method used

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  • Synthesis method of 13-methyl berberine alkaloid
  • Synthesis method of 13-methyl berberine alkaloid
  • Synthesis method of 13-methyl berberine alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of 13-methylberberine:

[0046]

[0047] Described step (a) concrete operation:

[0048] 1. After drying the double-necked bottle, add 4AMS powder under the protection of argon, then add 3,4-methylenedioxyphenethylamine and 2,3-dimethoxybenzaldehyde, and use it after drying After the solvent is dispersed evenly, it is placed at room temperature and stirred at 300-400r / min for 12 hours. After the reaction is complete as detected by TLC, the reaction solution is filtered with diatomaceous earth to remove molecular sieves, and the solution is spin-dried to obtain the crude Schiffer's base.

[0049]2. Take the double-neck bottle, after drying, disperse the crude Schiff base with a solvent under the protection of argon, put it in an ice bath to pre-cool, then slowly add sodium borohydride into it, and detect the reaction by TLC. The reaction solution was quenched with saturated ammonium chloride solution under ice bath, the organic solvent was spinned off, an...

Embodiment 2

[0055] Preparation of 13-methylpalmatine base:

[0056]

[0057] The operation in the step (a) is the same as in Example 1, except that arylethylamine is replaced by 3,4-dimethoxyphenethylamine.

[0058] The operation in step (b) is the same as in Example 1 to obtain a yellow solid with a yield of 91%.

[0059] Melting point: 169.3-171.4°C, 1 H NMR(400MHz,DMSO-d6)δ9.91(s,1H),8.21(s,1H),8.19(d,J=9.5Hz,1H),7.39(s,1H),7.18(s,1H) ,4.89–4.82(m,2H),4.11(s,3H),4.09(s,3H),3.89(s,3H),3.86(s,3H),3.14(d,J=5.9Hz,2H), 2.99(s,3H). 13 C NMR(151MHz,DMSO-d6)δ150.63,150.18,147.19,144.03,143.98,136.06,133.08,131.81,129.73,125.91,121.29,120.70,119.12,114.34,111.01,62.04,57.02,56.83,56.18,55.86,26.82 ,17.72

Embodiment 3

[0061] The preparation of 13-methyl coptisine:

[0062]

[0063] The operation in the step (a) is the same as in Example 1, the arylethylamine is 3,4-methylenedioxyphenethylamine, and the aromatic aldehyde is replaced by 2,3-methylenedioxybenzaldehyde.

[0064] The operation in step (b) is the same as in Example 1 to obtain a yellow solid with a yield of 87%.

[0065] Melting point: 231-232.7°C, 1 H NMR (400MHz, DMSO-d 6 )δ9.97(s,1H),8.05(d,J=8.9Hz,1H),7.98(d,J=8.9Hz,1H),7.46(s,1H),7.14(s,1H),6.56( s,2H),6.18(s,2H),4.78(t,J=5.9Hz,2H),3.15–3.06(m,2H),2.91(s,3H). 13 C NMR (101MHz, DMSO-d 6 )δ 148.93, 147.09, 146.36, 144.75, 143.09, 135.42, 133.71, 132.24, 130.74, 120.39, 120.12, 119.51, 110.84, 110.73, 108.16, 104.71, 102.01, 276.19

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 13-methyl berberine alkaloid. The method comprises the following steps: reaction a: taking arylethylamine and aryl formaldehyde as main starting raw materials, and reacting in the presence of other auxiliary materials to obtain secondary amine hydrochloride; and reaction b: taking secondary amine hydrochloride and pyruvic aldehyde as main raw materials, and reacting in the presence of other auxiliary materials to obtain the 13-methyl berberine alkaloid. According to the invention, aryl ethylamine and aryl formaldehyde are used as raw materials to synthesize secondary amine hydrochloride, and then the secondary amine hydrochloride and pyruvic aldehyde are subjected to Pickering-Schengger reaction/Friedel-Crafts hydroxyalkylation reaction/dehydration reaction/oxidation reaction in an anhydrous formic acid solution under the assistance of a dewatering agent and an oxidizing agent, so that the 13-methylberberine alkaloid is prepared at the yield of more than 80%, and the synthesis steps are simplified and easy to operate; and various expensive metal catalysts and excessive acid catalysis are not needed, the productivity is high, and the cost is low.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing 13-methylberberine alkaloids. Background technique [0002] The main source of 13-methylberberine alkaloids is the rhizome extract of Coptidis Rhizome, which is a C-13 methyl-substituted berberine derivative. Berberine is an important component of Coptis chinensis, a famous traditional Chinese herbal medicine. It has a history of more than 2,000 years and is widely distributed in plant tissues such as Coptis chinensis and Cortex Phellodendri. In-depth research on berberine has also led to research on 13-methyl berberine alkaloids, and recent studies have shown that it has a wide range of pharmacological activities, such as antibacterial, anti-inflammatory, anti-tumor, anti-obesity and anti-high cholesterol activity, and studies have shown that it can resist atherosclerosis. 13-Methyl-berberine alkaloids have good medicinal prospects. Extrac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03
CPCC07D455/03Y02P20/55
Inventor 陈芬儿唐培陈文昌蒋龙李亚玲
Owner SICHUAN UNIV
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