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A kind of preparation method of dihydroberberine

A technology of dihydroberberine and donor, which is applied in the field of preparation of dihydroberberine, can solve the problems of only 55% separation yield, increase of hydrolyzed impurities, excessive yield, etc., and achieve convenient and easy post-reaction treatment Good control and selectivity

Active Publication Date: 2020-06-16
NANJING NUTRABUILDING BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] 1) Pictet-Spengler reaction requires excessive aldehyde and low yield;
[0011] 2) Part of the acetal is hydrolyzed in the reductive ammoniation process, and the hydrolyzed impurities are greatly increased after amplification, resulting in a greatly reduced yield;
[0012] 3) According to literature reports, the separation yield of the intermediate dihydroberberine is only 55%, which is even lower during the amplification process

Method used

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  • A kind of preparation method of dihydroberberine
  • A kind of preparation method of dihydroberberine
  • A kind of preparation method of dihydroberberine

Examples

Experimental program
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Embodiment 1 2

[0029] The preparation of embodiment 1 dihydroberberine

[0030]

[0031] Under nitrogen protection, berberine hydrochloride (10g, 26.9mmol) was dissolved in 150mL of methanol, and 0.1g of 10% palladium carbon, ammonium formate (5.08g, 80.7mmol) and sodium bicarbonate (2.25g, 26.9mmol) were added at room temperature ). After the addition is complete, stir at 40-50°C for 5 hours, and TLC detects that the reaction is complete. After filtration, it was concentrated, slurried with water and then dried to obtain 8.9 g of yellow solid (molar yield: 98%). The liquid phase purity is 98%. 1 H NMR (300MHz, CDCl 3 )δ7.18(d,1H,J=8.7Hz),6.73(m,2H),6.56(s,1H),5.95(s,1H),5.94(s,2H),4.32(s,2H), 3.84(s, 6H), 3.20(t, 2H, J=8.1Hz), 2.90(t, 2H, J=8.1Hz).

Embodiment 2 2

[0032] The preparation of embodiment 2 dihydroberberine

[0033]

[0034] Under nitrogen protection, berberine nitrate (10 g, 25.1 mmol) was dissolved in 150 mL of isopropanol, and 0.1 g of Raney nickel and potassium carbonate (2.08 g, 15.1 mmol) were added at room temperature. After the addition is complete, stir at 70-80°C for 12 hours, and TLC detects that the reaction is complete. Concentrate after filtration, beat with water and dry to obtain 8.0 g of yellow solid (molar yield: 95%). The liquid phase purity is 98%.

Embodiment 3 2

[0035] The preparation of embodiment 3 dihydroberberine

[0036]

[0037] Berberine acetate (10 g, 25.2 mmol) was dissolved in 150 mL of tetrahydrofuran, and 0.1 g of 10% platinum on carbon and sodium hydroxide (1.1 g, 26.5 mmol) were added at room temperature. After the addition was completed, the mixture was stirred at 20-30° C. under normal pressure for 8 hours under a hydrogen atmosphere, and the reaction was detected by TLC. Concentrate after filtration, beat with water and dry to obtain 8.0 g of yellow solid (molar yield: 95%). The liquid phase purity is 98%.

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Abstract

The invention provides a preparation method of dihydroberberine. The preparation method comprises the following steps: in the presence of a catalyst, performing catalytic transfer hydrogenation on a compound (described in the specification) and a hydrogen donor in a certain solvent to obtain the compound (described in the specification) dihydroberberine. In the method, the raw material, berberinesalt, is cheap and easily available; reaction conditions are mild, the selectivity is good, and the yield is high; and intermediates and products are purified by crystallization to avoid column chromatography. The method disclosed by the invention is simple and easy to operate, stable in process, easy to control, easy to treat after reaction, high in product yield, and high in purity, and can be used in industrial production economically and conveniently.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of dihydroberberine. Background technique [0002] In recent years, berberine has been widely used clinically to treat type II diabetes. Studies have found that berberine can increase the uptake and utilization of glucose in human peripheral tissues (such as muscle) by activating AMPK protein, thereby reducing the blood sugar level of diabetic patients. Dihydroberberine was shown to be more potent than berberine against increased obesity, tissue triglyceride accumulation, and insulin resistance in mice fed a high-fat diet. In addition, studies have shown that dihydroberberine has potential antitumor activity. The structural formula of dihydroberberine is as follows: [0003] [0004] There have been research reports on the preparation method of dihydroberberine. The traditional method is the reduction of berberine with metal hyd...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D455/03
CPCC07D455/03
Inventor 张健廖琪林
Owner NANJING NUTRABUILDING BIO TECH CO LTD
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