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Preparation method of mestanolone

A technology of methionandrolone and androsterol, which is applied in the field of methionandrolone preparation, can solve the problems of reducing the production cost of methionandrolone, complex process operation, difficult sewage treatment, etc., and achieves industrial production, wide sources, and economical synthesis route The effect of environmental protection

Inactive Publication Date: 2017-11-03
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a new method for preparing nandrolone, which can solve many defects in the existing production process, such as expensive raw materials, difficult sewage treatment, complicated process operation, etc., and greatly reduce the production cost of nandrolone

Method used

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  • Preparation method of mestanolone
  • Preparation method of mestanolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A. Preparation of ether compounds

[0033] In a 1000ml three-neck flask, add 100g 4AD, 200ml ethanol, 80ml triethyl orthoformate, 2g p-toluenesulfonic acid, keep warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. After the reaction, add 3ml of pyridine, stirred for 20-25 minutes to neutralize the acid, then cooled the system to -5-0°C, stirred and crystallized for 2-3 hours, filtered with suction, washed with a small amount of ethanol, combined the lotion and filtrate, recovered the solvent and used the crude product; The cake was dried below 70°C to obtain 101.6 g of etherified compound, the HPLC content was 99.2%, and the weight yield was 101.6%.

[0034] B. Preparation of Grignard

[0035]In a 2000ml three-necked flask, add 20g of metal magnesium chips and 500ml of THF, heat up to 40-45°C, replace with nitrogen, then slowly introduce methyl bromide, and stir for 8-10 hours until the metal magnesium is completely reacted. After the ...

Embodiment 2

[0041] A. Preparation of ether compounds

[0042] In a 1000ml three-neck flask, add 100g 4AD, 600ml dichloromethane, 80ml triethyl orthoformate, 2g p-toluenesulfonic acid, keep warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. , add 3ml of pyridine, stir for 20-25 minutes to neutralize the acid, concentrate under reduced pressure, recover dichloromethane, lower the temperature, add 100ml of ethanol, then cool the system to -5-0°C, stir and crystallize for 2-3 hours, and filter with suction. A small amount of ethanol was washed, the washing liquid and the filtrate were combined, the solvent was recovered and the crude product was reused; the filter cake was dried below 70°C to obtain 100.2 g of ether compound, the HPLC content was 99.4%, and the weight yield was 100.2%.

[0043] B. Preparation of Grignard

[0044] In a 2000ml three-necked flask, add 20g metal magnesium chips and 500ml THF, raise the temperature to 40-45°C, replace with nitrog...

Embodiment 3

[0050] A. Preparation of ether compounds

[0051] In a 1000ml three-neck flask, add 100g 4AD, 200ml ethanol, 80ml triethyl orthoformate, 2g 98% sulfuric acid, keep warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. After the reaction, add 3ml of pyridine, stirred for 20-25 minutes to neutralize the acid, then cooled the system to -5-0°C, stirred and crystallized for 2-3 hours, filtered with suction, washed with a small amount of ethanol, combined the washing liquid and the filtrate, recovered the solvent and used the crude product; filtered The cake was dried below 70°C to obtain 100.8 g of etherified compound, the HPLC content was 99.0%, and the weight yield was 100.8%.

[0052] B. Preparation of Grignard

[0053] In a 2000ml three-neck flask, add 20g of magnesium metal chips and 500ml of ether, raise the temperature to 38-40°C, replace with nitrogen, slowly add methyl iodide dropwise, and stir for 8-10 hours until the metal magnesium reacts...

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Abstract

The invention relates to a preparation method of mestanolone. The preparation method comprises the following steps of adopting 4AD as a raw material, carrying out acid catalyzed reaction on the 4AD and triethyl orthoformate in an organic solvent such as lower alcohol to obtain etherate; carrying out grignard addition reaction on the etherate and a methyl-grignard-reagent in an organic solvent to obtain grignard which is 3-ethyoxyl-17a methyl-androstane-3,5-diene-17-alcohol; then catalyzing through palladium-charcoal, carrying out double-bond hydrogenation on a grignard 5 bit to obtain hydride which is 3-ethyoxyl-androstane-3 alkene-17-ketone, finally carrying out acid-catalyzed hydrolysis on the hydride in the organic solvent such as lower alcohol to obtain a mestanolone crude product, and then carrying out decoloration refining through ethyl alcohol and activated carbon to obtain the mestanolone. The HPLC content is 99.5 percent or more, the melting point is 192.5 to 194.0 DEG C, and the synthesis weight total yield is 76 to 83 percent. The preparation method provided by the invention is cheap and easily available in raw materials, simple and convenient in process operation, good in product purity, high in yield, high in solvent recovery rate, reduced in production cost by 25 to 30 percent, and favorable for industrial production.

Description

technical field [0001] The invention belongs to the preparation technology of steroid hormone drug intermediates, and in particular relates to a preparation method of metandrolone. Background technique [0002] Minandrolone is an important intermediate in the production of steroid hormone drugs. Using it as a raw material, many common androgen drugs such as Anadrol and Stanozolol can be produced. [0003] The traditional production method of minandrolone is to use the diosgenin extracted from the yam plant, through protection, oxidative cracking, and elimination, to obtain the acetic acid pregnant dienolone (referred to as diene) as the raw material, through oximation, rearrangement, Grignard, hydrogenation, alkali hydrolysis, oxidation and other six-step reaction, the process route is shown in the appendix figure 1 . Among them, the extraction of diosgenin, oxidative cracking, oximation of dienes, rearrangement, and the final step of chromic anhydride oxidation, etc., ha...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0037
Inventor 胡爱国甘红星吴来喜
Owner HUNAN KEREY BIOTECH
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