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Process for synthesizing high-content dehydronandrolon acetate

A technique for the synthesis of dehydronandrolone acetate, applied in the direction of steroids, organic chemistry, etc., to achieve the effects of simple synthesis process conditions, improved economic benefits, and high content

Inactive Publication Date: 2015-01-21
湖北三晶生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] According to the search, there is no patent application identical to the present invention in China

Method used

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  • Process for synthesizing high-content dehydronandrolon acetate
  • Process for synthesizing high-content dehydronandrolon acetate
  • Process for synthesizing high-content dehydronandrolon acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Step 1: Compound 2——Δ 3,5 - the preparation method of estro-3-acetoxy-17-one (2):

[0057] Take 1.0g (3.67mmol) of estro-4-ene-3,17-dione (1), add 5.0ml of acetic anhydride to make it just dissolve, then add 0.05g (0.17mmol) of p-toluenesulfonic acid, at 15°C After reacting for about 15 minutes, the reaction solution became turbid, and white solids precipitated out. After continuing the reaction for 2 hours, add 80ml of saturated sodium bicarbonate solution and stir for 1 hour. When the solids were dispersed in the solution in powder form, filter directly, wash the solids twice with water, and dry them in the air. Solid, to obtain off-white powdery solid Δ 3,5 -Estro-3-acetoxy-17-one (2) 1.12g, yield 97.2%, mp157-159°C;

[0058] Step 2: Compound 3—the preparation method of estra-3,5-diene-17β-alcohol-3-acetate (3):

[0059] Put 1.0g (3.18mmol) of compound 2 in the reaction vessel, add 30ml of methanol, but it cannot be dissolved completely, add 0.12g (0.32mmol) of po...

Embodiment 2

[0067] Step 1: Compound 2——Δ 3,5 - the preparation method of estro-3-acetoxy-17-one (2):

[0068] Take 1.0g (3.67mmol) estro-4-ene-3,17-dione (1), add 9.0ml isopropenyl acetate to make it just dissolve, then add 0.05g (0.17mmol) p-toluenesulfonic acid, dehydrate After reacting for 15 minutes, the reaction solution became turbid. Continue to react at room temperature for 1 hour, then add 80ml of saturated sodium bicarbonate solution and stir for 1 hour. When the solid is dispersed in the solution in powder form, filter directly, wash the solid with water twice, and dry the solid to obtain an off-white powder. solid Δ 3,5 -Estro-3-acetoxy-17-one (2) 1.12g, yield 97.2%, mp157-159°C;

[0069] Step 2: Compound 3—the preparation method of estra-3,5-diene-17β-alcohol-3-acetate (3):

[0070] Put 1.0g (3.18mmol) of compound 2 in the reaction vessel, add 30ml of methanol (not completely dissolved), and add 0.12g (0.32mmol) of sodium borohydride at 15°C, after 30min the reaction solut...

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Abstract

The invention provides a process for synthesizing high-content dehydronandrolon acetate. The process comprises the following five steps: 1, esterifying C-3 site of estr-4-ene-3,17-dione (1) serving as a starting raw material by using acetic anhydride under catalysis of toluenesulfonic acid to obtain a compound 2; 2, reducing carbonyl on the 17 site of the compound 2 into hydroxyl by using potassium borohydride at room temperature to obtain a compound 3; 3, reacting the compound 3 with NBS and DMF to obtain a compound 4; 4, reacting the compound 4 with lithium carbonate, lithium bromide and DMF to obtain a compound 5; 5, reacting the compound 5 with acetic anhydride and triethylamine to obtain the dehydronandrolon acetate. The synthesizing process is simple in condition, the industrial generation condition is easy to control, expensive reagent is not needed, consumption of reagent is reduced, production cost is reduced, and the 3-site carbonyl can be effectively controlled and protected; the process has short reaction route and low cost, is capable of improving yield and content, has a purity of over 99 percent (HPLC standard), and has remarkable comprehensive economic benefit. The process can be popularized and applied to all dehydronandrolon acetate production enterprises.

Description

technical field [0001] The invention relates to a synthesis process of dehydronandrolone acetate, in particular to a synthesis process for synthesizing high-content dehydronandrolone acetate by using estro-4-ene-3,17-dione as a starting material. Background technique [0002] Dehydronandrolonacetate (dehydronandrolonacetate) is a key intermediate in the synthesis of two steroid drugs, fulvestrant and tibolone. Fulvestrant is a new drug for the treatment of breast cancer. Tibolone It has long been used in the treatment of women's menopausal syndrome, and its chemical name is 17b-Acetyloxy-estra-4,6-diene-3-one17β-acetate, estro-4,6-diene-3-one, and its English name is Dehydronandrolonacetate. [0003] The synthetic technique of existing dehydronandrolone acetate has 3 kinds: [0004] 1. The synthesis process of dehydronandrolone acetate reported in patent WO2006015081 is: use nandrolone as raw material, use acetic anhydride and acetyl chloride for acylation reaction at the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0074
Inventor 尹宏程杏芳
Owner 湖北三晶生物科技股份有限公司
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