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Method for synthesizing high-yield nandrolone

A synthetic method and high-yield technology, applied in the direction of steroids, organic chemistry, etc., can solve the problems of many by-products, low quality, low yield, etc., and achieve the effect of improving yield and quality

Inactive Publication Date: 2013-04-03
YICHENG GOTO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional production process of nandrolone uses 19-norandrostenedione as raw material, reducing with potassium borohydride, and then oxidizing with manganese dioxide. This route has many by-products, low quality and low yield

Method used

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  • Method for synthesizing high-yield nandrolone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 1. Etherification reaction: In a 300L reactor equipped with stirring, meter 72 kg of absolute ethanol, 40 kg of triethyl orthoformate, and then add 75 kg of 19-norrostenedione while stirring, and stir 5 minutes; adjust the temperature in the reactor to 39-41°C, then add 0.3 kg of pyridinium hydrobromide, start the reaction, record the time for 8 hours, add 1.0 Kg of triethylamine after the reaction, cool down to 0-5°C, and Control the temperature at 0-5°C and keep stirring for 1 hour. When the reaction solution reaches neutrality, the etherification reaction is over, open the frozen brine, freeze and crystallize at 0±2°C; after the etherification reaction is terminated, release the etherification product from the reaction kettle, wash it with 98kg of absolute ethanol, Shake off filter to get wet ether compound.

[0019] 2. Reductive hydrolysis reaction: In a 1000L washed and dried reaction pot, first put 680 kg of methanol, start stirring, then put in 75 kg of ether co...

Embodiment 2

[0022] Embodiment 2: The used raw material and consumption of etherification reaction are changed, dehydrated alcohol 70kg, triethyl orthoformate 35kg, 19-norandrostenedione 70 kg, pyridinium hydrobromide 0.2 kg, triethylamine 0.6 kg;

[0023] The used raw materials and consumption of reduction hydrolysis reaction are changed into, methanol 650kg, ether compound 70kg, sodium borohydride 5kg;

[0024] The mass ratio of raw materials involved in crude product refining is 60kg of nandrolone crude product, 28kg of ethyl acetate, and 35kg of petroleum ether.

[0025] All the other are with embodiment 1.

Embodiment 3

[0026] Embodiment 3: the used raw material of etherification reaction and consumption change, dehydrated alcohol 75kg, triethyl orthoformate 45kg, 19-norandrostenedione 80 kg, pyridinium hydrobromide 0.5 kg, triethylamine 1.5 kg;

[0027] The used raw materials and consumption of reduction hydrolysis reaction are changed into, methanol 700kg, ether compound 80kg, sodium borohydride 10kg;

[0028] The mass ratio of raw materials involved in crude product refining is 65-68 kg of nandrolone crude product, 35 kg of ethyl acetate, and 45 kg of petroleum ether.

[0029] All the other are with embodiment 1.

[0030] The product of embodiment 1~3 and quality purity are shown in the following table:

[0031]

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PUM

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Abstract

The invention relates to a method for synthesizing high-yield nandrolone. The method comprises the following synthesizing steps of: (1) etherification reaction: absolute ethyl alcohol and triethyl orthoformate are put into a reactor which is provided with an agitation device to be agitated, 19-norandrostendione, and pyridine hydrobromate and triethylamine are then put into the reactor and are agitated, freeze crystallized, sprinkled and centrifugally filtered to obtain wet etherate; (2) reduction hydrolysis reaction: in a reaction vessel, methanol is put at first to be mixed, the etherate and sodium borohydride are then put, acid is added to regulate pH, vacuum concentration is carried out, water is flushed, centrifugation is carried out to obtain a reduction hydrolysate, i.e. crude nandrolone, and the crude nandrolone is dried; and (3) crude product refining: the crude nandrolone, ethyl acetate and petroleum ether are put into a tank at one time and are heated to dissolve, cooled, centrifuged and dried, so that refined nandrolone is obtained. The method adopts a new catalyst-pyridine hydrobromate, so that a hydrolysis phenomenon cannot be caused after protection materials are added, and thus, the protection yield and quality are improved.

Description

technical field [0001] The invention relates to a synthesis method of nandrolone, in particular to a synthesis method of nandrolone with high yield. Background technique [0002] Nandrolone, as a stimulant, is mainly used for nutritional deficiencies and emaciation in the elderly, for people with severe burns and operations, and can promote muscle growth and development, increase training endurance and training load. The traditional production process of nandrolone uses 19-norandrostenedione as raw material, reduction with potassium borohydride, and oxidation with manganese dioxide. This route has many by-products, low quality and low yield. CN101456888A discloses "a kind of preparation method of primobolan", which uses isotestosterone acetate as a raw material, protonic acid as a catalyst, and through ketal oxidation reaction and Grignard reaction, a kind of primobolone is prepared, and the method is only The existing primobolone is converted into primobolan acetate and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 薛文武系祖斌刘卫东王延贞
Owner YICHENG GOTO PHARMA
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