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Preparation method and application of steroid intermediate

A technology for intermediates and steroids, which is applied in the field of preparation of steroid intermediates, can solve the problems of high cost of oxidizing reagent Dess Martin, difficult to realize industrialized production, and many reaction by-products, etc., and achieves improved production applicability and easy control. , the effect of increasing the reaction temperature

Pending Publication Date: 2022-04-12
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The disadvantage of using this route is that the product yield is low, the oxidation reagent Dess Martin is expensive, and there are many reaction by-products. This method is not easy to realize industrial production

Method used

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  • Preparation method and application of steroid intermediate
  • Preparation method and application of steroid intermediate
  • Preparation method and application of steroid intermediate

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Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0084]

Embodiment 1-1-1

[0086] 15.0 g of Compound I-a and 75 mL of dichloromethane were added to the reaction flask, and stirred at room temperature to dissolve. Add 0.5g of potassium bromide, 1.0g of sodium bicarbonate, 0.04g of TEMPO and 7.5mL of water, stir to cool down to -5-0°C, start adding 16.9g of calcium hypochlorite in portions, control the temperature at 0°C, and complete the addition in about 30 minutes , insulated and stirred for 1 h, and no compound I-a was detected by TLC. Add 36 mL of an aqueous solution of sodium thiosulfate under an ice bath, return to room temperature and stir for 30 min, let the layers stand, wash with water, separate the organic layer, dry, filter, and concentrate under reduced pressure to obtain 14.6 g of compound II-a with a molar yield of 93.5%. HPLC purity 99.8%.

Embodiment 1-1-2

[0088] 15.0 g of Compound I-a and 75 mL of acetonitrile were added to the reaction flask, and stirred at room temperature to dissolve. Add 0.9g of sodium bromide, 0.9g of potassium bicarbonate, 0.07g of TEMPO and 7.5mL of water, stir and cool down to -10~-5°C, start adding 5.1g of sodium hypochlorite in portions, control the temperature at 5°C, finish adding for about 30 minutes, and keep warm The reaction was stirred for 1 h, and no compound I-a was detected by TLC. Add 36 mL of an aqueous solution of sodium thiosulfate under an ice bath, return to room temperature and stir for 30 min, let the layers stand, wash with water, separate the organic layer, dry, filter, and concentrate under reduced pressure to obtain 14.1 g of compound II-a with a molar yield of 90.3%. HPLC purity 95.2%.

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Abstract

The invention provides a preparation method and application of a steroid compound intermediate, and relates to the technical field of chemical synthesis. Comprising the following steps: (a) carrying out oxidation reaction on a compound I under the action of a TEMPO catalyst, pypocholoride and an alkali reagent to obtain a compound II; (b) the compound II is subjected to an oxidative decarboxylation reaction under the action of a Schiff base metal complex, an oxidizing agent and organic alkali, and a compound III is obtained. According to the method, a brand new synthesis route is adopted, the reaction time is shortened, the reaction temperature is increased, a reagent with high toxicity and high odor in an original route is avoided, meanwhile, an oxidizing agent with high cost is also avoided, the reaction condition is milder and easy to control, and the production applicability is improved.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method and application of a steroid intermediate. Background technique [0002] Steroid hormone drugs (steroid hormone drugs) refer to hormone drugs containing steroidal structure in their molecular structure, which are widely used clinically and mainly include adrenocortical hormones and sex hormones. Among them, adrenal cortex hormone has various pharmacological effects such as anti-inflammation, anti-allergy, immune suppression, enhancement of stress response, anti-endotoxin and anti-shock. Such as cortisone, hydrocortisone corticosteroids. Sex hormones include progesterone, estrogen and androgen, such as finasteride, a 4-aza steroid compound, which is mainly used clinically to treat benign prostatic hyperplasia and male pattern hair loss. [0003] Pregn-4-ene-3,20-dione (progesterone) and its derivatives are an important class of steroid hormone int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00C07J7/00C07J73/00
Inventor 张彦巧袁翠翠杨娣郭朋朋孟庆礼
Owner TIANJIN PHARMA GROUP CORP
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