Synthetic method of androstenone

A synthetic method and technology of androstenone, applied in the field of pharmaceutical preparation, can solve the problems of industrial production limitation and low yield

Active Publication Date: 2021-05-11
厦门欧瑞捷生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In order to solve the problems of low yield, dangerous reagents and the use of heavy metal chromium in the existing androstenone synthesis method, which restrict its industrial production and limit its application range

Method used

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  • Synthetic method of androstenone
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  • Synthetic method of androstenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] 1. Preparation of Compound I

[0089] In the autoclave of 10L, add testosterone respectively, namely testosterone (1000g, 3.472mol), methanol (5000mL, 5v / w) and 50g palladium carbon (50% water content, 5% palladium content), nitrogen replacement protection, then Start stirring and cool down to ≤-20°C, then replace nitrogen with hydrogen, keep the pressure in the kettle at 0.2MPa, and react at constant temperature and pressure for 8 hours. After the reaction is monitored by TLC, nitrogen is used for three times, and then the material is withdrawn and recovered by filtration The catalyst and filter cake were washed with methanol, the combined filtrates were concentrated under reduced pressure to recover methanol, and then vacuum-dried to ensure that the methanol content was less than 1% to obtain compound I crude product, white solid (1000 g, crude product yield 99%).

[0090] 2. Preparation of the target product androstenone

[0091] Compound I (500g, 1.724mol) and trie...

Embodiment 2

[0098] 1. Preparation of Compound I

[0099] In the autoclave of 10L, add testosterone respectively, namely testosterone (1000g, 3.472mol), methanol (5000mL, 5v / w) and 50g palladium carbon (50% water content, 5% palladium content), nitrogen replacement protection, then Start stirring and cool down to ≤-20°C, then replace nitrogen with hydrogen, keep the pressure in the kettle at 0.2MPa, and react at constant temperature and pressure for 8 hours. After the reaction is monitored by TLC, nitrogen is used for three times, and then the material is withdrawn and recovered by filtration The catalyst and filter cake were washed with methanol, the combined filtrates were concentrated under reduced pressure to recover methanol, and then vacuum-dried to ensure that the methanol content was less than 1% to obtain compound I crude product, white solid (1000 g, crude product yield 99%).

[0100] 2. Preparation of the target product androstenone

[0101] Compound I (500g, 1.724mol) and trie...

Embodiment 3

[0103] 1. Preparation of Compound I

[0104] In the autoclave of 10L, add testosterone respectively, namely testosterone (1000g, 3.472mol), methanol (5000mL, 5v / w) and 50g palladium carbon (50% water content, 5% palladium content), nitrogen replacement protection, then Start stirring and cool down to ≤-20°C, then replace nitrogen with hydrogen, keep the pressure in the kettle at 0.2MPa, and react at constant temperature and pressure for 8 hours. After the reaction is monitored by TLC, nitrogen is used for three times, and then the material is withdrawn and recovered by filtration The catalyst and filter cake were washed with methanol, the combined filtrates were concentrated under reduced pressure to recover methanol, and then vacuum-dried to ensure that the methanol content was less than 1% to obtain compound I crude product, white solid (1000 g, crude product yield 99%).

[0105] 2. Preparation of the target product androstenone

[0106] Compound I (500g, 1.724mol) was diss...

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Abstract

The invention relates to the field of medicine preparation, in particular to a synthetic method of androstenone. The preparation method comprises the following steps: S100, catalyzing testosterone by a catalyst, and carrying out hydrogenation addition reaction to obtain a compound I; S200, converting a 17-site hydroxyl group of the compound I into a halogen group or a sulfonate group which is easy to leave, so as to obtain a compound II; and S300, subjecting the compound II and alkali to an elimination reaction under the heating condition, namely, a dehalogenation reaction or a desulphonate reaction, so as to obtain androstenone. The synthesis method of androsteneone has the following beneficial effects: the raw materials are cheap and easy to obtain; the process is simple, the route is short, and the requirement on equipment is low; dangerous reagents and operation are avoided, and large-scale industrial production is easy to realize; and isomer impurities are not generated in the synthesis process, and the yield of the target product androsteneone is high.

Description

technical field [0001] The invention relates to the field of pharmaceutical preparation, in particular to a method for synthesizing androstenone. Background technique [0002] Androstenone is a steroid compound commonly known as Androstenone in English. It is also known as swine ketene or androstenone. It is a sexual pheromone of pigs. It exists in large quantities in the saliva of uncastrated boars. It is the main source of odor in boars. When androstenone is used, it will arch its back to prepare for mating. This androstenone plays an important role in the mating and reproduction of pigs. It is an active ingredient in the artificial insemination product "Zhuyuling" that tests whether sows are in estrus. . And androstenone also exists in human sweat and urine as well as in the cytoplasm of celery. It is a compound with a strong musk fragrance and is a pheromone of mammals. will have effects and effects. [0003] At present, the method for synthesizing androstenone mainl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J13/00
CPCC07J13/005
Inventor 李刚万明郑飞剑张江平李勇杰魏积福赵哲峰郑扶桑王萍
Owner 厦门欧瑞捷生物科技有限公司
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