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Preparation method of 19-nor-4-androstenedione

A technology of androstenedione and compound is applied in the field of preparation of 19-nor-4-androstenedione, can solve the problems of low yield, many impurities, difficult to purify into white, etc., achieves improved yield and Purity, low refining cost, easy decolorization and refining effect

Pending Publication Date: 2022-03-18
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The yield of the above-mentioned reduction and ring closure reaction is not high, only about 55%, the purity is about 97%, and the product is off-white to light yellow, with many impurities, it is difficult to purify it into white

Method used

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  • Preparation method of 19-nor-4-androstenedione
  • Preparation method of 19-nor-4-androstenedione
  • Preparation method of 19-nor-4-androstenedione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 100g of compound A, 1000g of ethanol, and 3g of pyridine were stirred and dissolved, and put into a high-pressure hydrogenation kettle. After the kettle was replaced with nitrogen three times, 3g of palladium carbon was dropped into the kettle (the weight content of palladium was 5%). Open the vacuum valve, evacuate to the pressure in the autoclave ≤ -0.08Mpa, open the hydrogen to positive pressure; repeat the operation again, open the hydrogen valve, and pressurize the autoclave to 0.1MPa. The temperature in the kettle was raised to 60°C for reaction, and after the temperature of the system became stable, the pressure of the reaction kettle was increased again and maintained to 0.3MPa. After the reaction of the raw materials was completed, the temperature of the reaction system was lowered to room temperature 25°C, the pressure of the reaction kettle was first slowly released to normal pressure, and then the system was replaced with nitrogen for 15 minutes. The system...

Embodiment 2

[0030] The preparation method of Compound C wet product is the same as in Example 1.

[0031] Add 50g of isopropanol and 150g of water to the wet product of compound C, then add 80g of sodium bisulfate solution (weight concentration: 30%), the system is heated up to 80°C to form a ring reaction, after the reaction is complete, cool down to 60°C, and slowly add 1.5kg Water analysis was carried out with tap water, the temperature of the system was lowered to 10° C., filtered, and washed with water to obtain crude 19-nor-4-androstenedione (acidic decarboxylation product). The crude product was dissolved in 600 g of methanol and 5 g of activated carbon, decolorized and recrystallized to obtain the refined product of 19-nor-4-androstenedione (acidic decarboxylation product). The total yield is 64%, the purity is 99.4%, and the product color is white.

Embodiment 3

[0033] The preparation method of the ethanol solution of Compound B is the same as in Example 1.

[0034] The ethanol solution of Compound B was concentrated under negative pressure at 50°C (vacuum ≤ -0.08Mpa), replaced once with 100 g of water, and concentrated again until no distillate was present to obtain the wet product of Compound B.

[0035] Add 300g of isopropanol to the wet product of compound B, then add 45ml of concentrated hydrochloric acid, the system is heated up to 50°C to form a cyclic reaction, after the reaction is completed, 1.8kg of tap water is slowly added for water analysis, the system is cooled to 10°C, filtered, and washed with water to obtain 19- Nor-4-androstenedione (acid decarboxylation) crude product. The crude product was dissolved in 600 g of ethanol and 5 g of activated carbon, decolorized and recrystallized to obtain the refined product of 19-nor-4-androstenedione (acidic decarboxylation product). The total yield is 63%, the purity is 99.3%, ...

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Abstract

The invention belongs to the technical field of steroid hormone preparation, and particularly relates to a preparation method of 19-nor-4-androstenedione, which comprises the following steps: mixing a compound A, ethanol and pyridine, adding palladium on carbon, introducing hydrogen, and reacting to obtain a compound B; the compound B and isopropanol are mixed, an acid solution is added, the acid solution is a hydrochloric acid solution or a salt solution of alkali metal which is dissolved to be acidic, reaction and treatment are conducted, and 19-nor-4-androstenedione is obtained, the reaction route is as follows: the yield and purity of the product can be effectively improved, and the product is white.

Description

technical field [0001] The invention belongs to the technical field of steroid hormone preparation, and in particular relates to a preparation method of 19-nor-4-androstenedione. Background technique [0002] The Chinese patent application No. CN201410839930.6 discloses a preparation method of 19-nor-4-androstene-3,17-dione, using compound I as raw material, through Grignard reaction, oxidation and ring closure reaction , reduction and ring-closing reaction to prepare, the reaction scheme is as follows: [0003] [0004] Reduction and ring closure reactions include the following steps: [0005] (a) Add compound III in the fifth organic solvent, drop into palladium carbon, feed hydrogen gas, after reaction, obtain intermediate solution, the fifth organic solvent is toluene, ethanol, n-propanol, isopropanol and acetone one or more; the reaction temperature is 0°C to 50°C; the mass ratio of compound III, palladium carbon, and the fifth organic solvent is 1:0.01 to 1:1 to 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0059
Inventor 吴亚克曾春玲刘喜荣刘家贝文智彬
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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