Synthesis method of trenbolone acetate

A technology of trenbolone acetate and a synthetic method, which is applied in the field of androgen preparation, can solve problems such as ineffective technical and economical effects, and achieve the effects of optimizing reaction routes and processes, reducing raw material costs, and reducing production costs

Active Publication Date: 2018-05-11
ZHEJIANG XIANJU JUNYE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, simply exchanging the last two steps has no obvious effect on improving the technical economy of the reaction route. Based on the above-mentioned defects in the prior art, a new method that can increase product yield, reduce production cost and discharge of three wastes will continue to be provided. New trenbolone acetate production process becomes a problem to be solved urgently in the prior art

Method used

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  • Synthesis method of trenbolone acetate
  • Synthesis method of trenbolone acetate
  • Synthesis method of trenbolone acetate

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Step 1) reduction reaction:

[0027] 20kg of 4,9-ring-opened compound (I) was dissolved in 200kg of methanol, and 3kg of potassium borohydride was added in portions at 20-25°C. After the addition was completed, the reaction was incubated for 2 hours. TLC analysis of the reaction of the raw materials was complete to obtain compound (II).

[0028] Step 2) hydrolysis reaction

[0029] Add dilute acid (5.4kg sulfuric acid+25kg water) dropwise to the reaction system that has completed the reaction of step 1), neutralize to PH=7, prepare dilute sulfuric acid (7kg sulfuric acid+50kg water), prepare and cool to room temperature, and control the reaction system Temperature 20-25°C, add dilute sulfuric acid dropwise to the above reaction system, after dropping, stir for 2 hours, TLC analysis of raw material reaction is complete, add the reaction solution into sodium carbonate aqueous solution (14kg sodium carbonate + 140kg water) for water analysis, continue stirring 30min until...

Embodiment 2

[0035] Step 1) reduction reaction:

[0036] 20kg of 4,9-ring-opened compound (I) was dissolved in 300kg of methanol, and 5kg of potassium borohydride was added in portions at 20-25°C. After the addition was completed, the reaction was incubated for 2 hours. TLC analysis of the reaction of raw materials was complete to obtain compound (II).

[0037] Step 2) hydrolysis reaction

[0038] In the reaction system that has completed the reaction of step 1), add dropwise dilute acetic acid with a mass percentage concentration of 20% to neutralize to PH=7, prepare dilute sulfuric acid (8kg sulfuric acid+57kg water), prepare and cool to room temperature, and control the temperature of the reaction system at 20 ~25°C, add dilute sulfuric acid dropwise to the above reaction system, after dropping, stir the reaction for 2 hours, TLC analysis of raw material reaction is complete, add the reaction solution into sodium carbonate aqueous solution (15kg sodium carbonate + 150kg water) for water...

Embodiment 3

[0044] Step 1) reduction reaction:

[0045] 20kg of the 4,9-ring-opened compound (I) was dissolved in 160kg of methanol, and 3kg of potassium borohydride was added in portions at 20-25°C. After the addition was complete, the reaction was incubated for 2 hours. TLC analysis of the reaction of the raw materials was complete to obtain compound (II).

[0046] Step 2) hydrolysis reaction

[0047] Add dilute sulfuric acid with a mass percentage concentration of 15% to the reaction system that has completed the reaction of step 1) to neutralize to PH=7, and prepare dilute sulfuric acid (6kg sulfuric acid+44kg water) in addition, and cool it down to room temperature after mixing, and control the temperature of the reaction system 20~25°C, add dilute sulfuric acid dropwise to the above reaction system, after dropping, stir and react for 2 hours, TLC analysis of raw material reaction is complete, add the reaction solution into sodium carbonate aqueous solution (15kg sodium carbonate + 1...

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Abstract

The invention provides a synthesis method of trenbolone acetate. The synthesis method comprises the following steps: step 1), dissolving a 4,9 ring-opening object (I) into methanol; adding potassium borohydride fractionally at 20 to 25 DEG C; after adding the potassium borohydride, carrying out heat preservation and reacting until a TLC (Thin-Layer Chromatography) analysis raw material is completely reacted, so as to obtain a compound (II); step 2), adding diluted acid into a reaction system for finishing reaction of step 1) and regulating the pH (Potential of Hydrogen) value to be neutral; dropwise adding dilute sulfuric acid and carrying out water separation to obtain 17beta-hydroxy-estra-5(10),9(11)-diene-3-one (III); step 3) dissolving the compound (III) into dichloromethane and addingDDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) and completely reacting; filtering; washing filtrate and combining a water layer; extracting the water layer by the dichloromethane; combining all dichloromethane layers; dehydrating, vacuum concentrating and drying to obtain trenbolone (IV); step 4) dissolving the trenbolone (IV) into the dichloromethane; adding DMAP (4-dimethylamiopryidine) and acetic anhydride and completely reacting to obtain the trenbolone acetate.

Description

technical field [0001] The invention relates to a preparation method of androgen. Background technique [0002] Trenbolone acetate is an anabolic hormone. The traditional production process of trenbolone acetate uses 4.9(11)-diene androster 3-17-dione (ADD) as raw material, p-toluenesulfonic acid or acetyl chloride as The catalyst is used to protect the 3-position carbonyl group, and then take reduction, dehydrogenation, and hydrolysis to obtain trenbolone; finally, trenbolone is esterified with acetic anhydride to obtain trenbolone acetate. This route has many by-products, low quality and low yield. [0003] Document 1 presents the preparation method of high-yield synthesis of trenbolone acetate (Fudan Journal Medical Edition, Volume 29, No. 3, 2002, pages 211-212), disclosing a preparation method of trenbolone acetate, 4, 9 (Estra-4,9-diene-3,17-dione, CAS: 5173-46-6) as raw material, through 3-dimethyl etherification, 17-position reduction, 3-position hydrolysis, 11,12 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0074
Inventor 徐思虎张峥斌胡明辉泮宝峰
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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