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Method of synthesizing testosterone through 4-androstenedione one-step method

A technology for androstenedione and testosterone is applied in the field of one-step synthesis of testosterone from 4-androstenedione, and can solve the problems of unstable oxidation activity of manganese dioxide, an oxidant activity, the need for optimization of testosterone synthesis yield, and increased side reactions, Achieve the effect of low cost, obvious market competition and improved reaction selectivity

Active Publication Date: 2015-01-07
JIANGSU JIAERKE PHARMA GRP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process has many reaction steps, and because the oxidation activity of oxidant active manganese dioxide is unstable and the end point of selective oxidation is difficult to control, the side reactions increase and the total yield is not high.
[0009] Judging from the existing technology, the synthesis yield of testosterone and the control of impurities still need to be optimized

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Step 1: Put 30g of androstenedione in a mixed solvent (dichloromethane: tetrahydrofuran = 1:1) with 10 times the weight of androstenedione, and cool to -15°C.

[0026] Step 2: Dissolve 3g of potassium borohydride in 30ml of distilled or pure water.

[0027] Step 3: Add the potassium borohydride aqueous solution obtained in the second step to the reaction system at -8°C obtained in the first step with a peristaltic pump at a flow rate of 0.2 ml / min.

[0028] Step 4: After adding, react at -5°C to -10°C until the reaction of androstenedione is complete (HPLC tracking), add 1g of glacial acetic acid to destroy excess potassium borohydride, recover the solvent by rotary evaporation, add 450ml of distilled water, and cool to 10°C, filtered, washed with water, and dried under vacuum to obtain a crude product.

[0029] Step 5: Dissolve the crude product with 10 times the weight of absolute ethanol, add 5wt% activated carbon for decolorization, filter while hot, concentrate un...

Embodiment 2

[0033] A method for synthesizing testosterone that can improve the yield of testosterone and significantly reduce impurities, comprising the steps of:

[0034] Step 1, dissolving androstenedione in a mixed solvent system of 5 times (weight ratio), cooling to below -10°C;

[0035] Step 2, potassium borohydride is dissolved in 8 times (weight ratio) of pure water;

[0036] Step 3, add the solution prepared in step 2 to the feed solution obtained in step 1 at 10 times (weight ratio) at -7°C; specifically, add the prepared solution to the obtained solution in step 1 at a rate of 0.2ml / min with a peristaltic pump in the liquid;

[0037] Step 4, after adding, react at -7°C until the reaction of androstenedione is complete (using HPLC tracking), add glacial acetic acid with a weight of 15% of the potassium borohydride to destroy excess potassium borohydride, and then Recover the solvent under reduced pressure, add water (10 times the weight of androstenedione), filter, and dry the ...

Embodiment 3

[0040] A method for synthesizing testosterone with 4-androstenedione one-step method with high product yield and simple aftertreatment, comprising the steps:

[0041] Step 1, dissolving androstenedione in a mixed solvent system of 15 times (weight ratio), cooling to below -10°C;

[0042] Step 2, potassium borohydride is dissolved in pure water of 14 times (weight ratio);

[0043] Step 3, add the solution configured in step 2 to the feed solution obtained in step 1 at 15 times (weight ratio) at -5°C; specifically, add the configured solution to the solution obtained in step 1 at a rate of 0.5ml / min with a peristaltic pump in the liquid;

[0044] Step 4, after adding, react at -9°C until the reaction of androstenedione is complete (tracked by HPLC), add glacial acetic acid with a weight of 35% of the potassium borohydride to destroy excess potassium borohydride, and then Recover the solvent under reduced pressure, add water (18 times the weight of androstenedione), filter, and...

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Abstract

The invention provides a method of synthesizing testosterone through the 4-androstenedione one-step method. The method is characterized by comprising the following steps: Step 1, dissolving androstenedione in a mixed solvent system which is 4-14 times heavier than the androstenedione in weight, and cooling the mixture below minus 10 DEG C; Step 2, dissolving potassium borohydride in purified water which is 7-14 times heavier than potassium borohydride in weight; Step 3, adding the solution prepared in the Step 2 to the feed liquid which is obtained in the Step 1, 4-14 times heavier than the androstenedione and is at minus 5 to minus 10 DEG C; Step 4, taking a reaction at a condition of minus 5 to minus 10 DEG C until androstenedione is completely reacted, adding glacial acetic acid which is 15-40% of the weight of the potassium borohydride to demage excessive potassium borohydride, reducing the pressure, recovering the solvent, adding water, filtering and obtaining a crude product; Step 5, recrystallizing the crude product with ethanol to obtain the finished testosterone product.

Description

technical field [0001] The invention relates to a method for synthesizing testosterone with 4-androstenedione in one step. Background technique [0002] Testosterone (Testosterone) is used for the replacement treatment of testicles, male menopausal syndrome, impotence and other diseases. It also has the effects of enhancing libido, strength, immune function, and fighting osteoporosis. [0003] According to literature reports, the synthesis of testosterone is to use dienolone acetate as a raw material, and obtain 4-androstenedione through oximation, Belleville reaction, hydrolysis, and Woshi oxidation, and then obtain through reduction and selective oxidation. From 4-androstenedione, the yield was 70.8%. The process has many reaction steps, and because the oxidation activity of the oxidant active manganese dioxide is unstable and the end point of selective oxidation is difficult to control, the side reactions increase and the total yield is not high. Zheng Shihui et al....

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0018C07J1/0022
Inventor 吴卫忠蒋澄宇
Owner JIANGSU JIAERKE PHARMA GRP CORP
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