Preparation method of 9β, 10α-pregna-4,6-diene-3,20-dione

A technology of diketone and diene, which is applied in the field of preparation of steroidal compounds, can solve problems such as low yield, low total yield, and difficulty in obtaining

Active Publication Date: 2020-03-31
TAIZHOU HISOUND PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the whole production process, because pregna-5-en-3β-ol-20-one itself is difficult to obtain, and dibromoheinin is needed in the production process, which is not friendly to the environment, which eventually leads to the pregnancy of raw materials in this route. Ste-5,7-diene-3β-ol-20-one is difficult to obtain
Secondly, the yield of each step reaction is not very high, resulting in lower total yield
Third, a large amount of 37% hydrogen chloride-isopropanol solution is used in the isomerization step, whi...

Method used

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  • Preparation method of 9β, 10α-pregna-4,6-diene-3,20-dione
  • Preparation method of 9β, 10α-pregna-4,6-diene-3,20-dione
  • Preparation method of 9β, 10α-pregna-4,6-diene-3,20-dione

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of compound B

[0032] Under the protection of nitrogen, put 22g of 9β,10α-pregna-5,7-diene-3,20-dione diethylene diacetal (compound A) into 500mL of ethanol, add dropwise 40mL of 8.5% dilute sulfuric acid. After the dropwise addition, the mixture was refluxed for 1 h under the protection of nitrogen. After the reaction was completed, it was added to the ice-water mixture, filtered, and dried to obtain 16.2 g of compound B, melting point: 145-147°C, yield 94.40%, and content about 97.2%.

[0033] Take 4g of compound B and recrystallize twice with acetone-water to obtain about 2.0g of light yellow crystals, melting point: 147.5~148℃, specific rotation: [α] D 25 =+106~+114°, content: 99.21%.

[0034] IR: 870, 1232, 1419, 1464, 1618, 1663, 1701, 2965, 3464cm -1 .

[0035] 1 H NMR (δ, ppm, CDCl 3 ): 0.55(s,3H); 1.01(s,3H); 1.39-1.43(m,1H); 1.55-1.80(m,6H); 1.96-1.99(m,1H); 2.08(s,3H); 2.16-2.18 (m, 3H); 2.32-2.46 (m, 3H); 2.63-2.67 (m,...

Embodiment 2

[0037] Embodiment 2: the preparation of compound B

[0038] Under the protection of nitrogen, put 3g of compound A into 50ml of 50% acetic acid, stir and react at 60-65°C for 30min, then pour it into a large amount of ice water, filter to obtain the crude product, and recrystallize from acetone-water to obtain 1.8g of compound, B Melting point: 147-148°C. About 0.36 g of compound B was recovered from the mother liquor, melting point: 146-147.5°C. The total yield is about 92.31%.

Embodiment 3

[0039] Embodiment 3: the preparation of compound B

[0040] Put 5.0g of Compound A into 75mL of dichloromethane, add 25ml of 5% hydrochloric acid dropwise at 0-5°C, keep warm and stir for 1h, then pour it into a large amount of ice water, stir for 10min, then let stand to separate layers, and the water layer Extract again with 75 ml of dichloromethane. The dichloromethane layers were combined and washed with saturated NaHCO 3 After the aqueous solution was washed twice, it was concentrated under reduced pressure and dichloromethane was evaporated to dryness to obtain 3.7 g of compound B, melting point: 146.2-147.8°C, yield about 94.87%.

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Abstract

The present invention relates to a method for preparing 9β,10α-pregnane-4,6-diene-3,20-dione. The preparation method uses 9β,10α-pregnane-5,7-diene-3,20-dione diethyl diacetal (compound A) as a raw material, which is deprotected under acidic conditions to give 9β,10α-pregnane-4,7-diene-3,20-dione (compound B), which then undergoes rearrangement under alkaline conditions to give 9β,10α-pregnane-4,6-diene-3,20-dione (compound C). The method of the present invention is simple, environmentally-friendly and has a very high yield.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound, in particular to a preparation method of 9β, 10α-pregna-4,6-diene-3,20-dione. Background technique [0002] 9β,10α-pregna-4,6-diene-3,20-dione, also known as Dydrogesterone and Dydrogesterone, has a melting point of 169-170°C and is white or light yellow crystalline powder at room temperature , Insoluble in water, soluble in ethanol, acetone, etc. Dehydroprogesterone, as a progestin drug, has obvious advantages and safety compared with other similar drugs, and is the drug of choice for the treatment of amenorrhea, endometriosis, prevention of functional bleeding and threatened abortion. Among the currently clinically applied synthetic progestogens, dehydroprogesterone is superior to other similar drugs, and is an effective and orally active synthetic progesterone drug. After more than 40 groups of clinical trials, it has been used in the treatment of tens of millions of women. It ha...

Claims

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Application Information

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IPC IPC(8): C07J75/00C07J7/00
CPCC07J15/005C07J21/006
Inventor 董军国吴志平陈济谷
Owner TAIZHOU HISOUND PHARMA CO LTD
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