Method for synthesizing 9beta,10alpha-dehydroprogesterone ketal through photochemical isomerization in micro-channel reactor

A technology of microchannel reactor and photochemical isomerization, which is applied in chemical instruments and methods, chemical/physical/physical chemical processes, chemical/physical/physical chemical reactors, etc. Low mass and heat transfer efficiency, unstable light and other problems, to achieve the effect of inhibiting the formation of by-products of photoisomerization reaction, convenient and feasible industrial production, and long service life of light source

Inactive Publication Date: 2021-01-29
JIANGSU ALPHA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the synthetic route of progesterone, there are many reports on the step of photochemically synthesizing 9β, 10α-dehydroprogesterone ketal with the intermediate 9α, 10β-dehydroprogesterone ketal as raw material. The main problem lies in the requirement of light for this step Extremely harsh, the coexistence of multiple reversible reactions causes the main product to be easily converted into by-products; and 9α, 10β-dehydroprogesterone ketal produces a large number of intermediates during the ring-opening process, and only by accurately controlling the ring-closing process can more 9β be obtained , 10α-Dehydroprogesterone Ketal
In this regard, people usually use two-stage reaction conditions, and use different wavelengths to open the ring to obtain intermediates and intermediates. , 10α-dehydroprogesterone ketal, obtained a higher yield (75.5%, based on the consumption of raw materials),...

Method used

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  • Method for synthesizing 9beta,10alpha-dehydroprogesterone ketal through photochemical isomerization in micro-channel reactor
  • Method for synthesizing 9beta,10alpha-dehydroprogesterone ketal through photochemical isomerization in micro-channel reactor

Examples

Experimental program
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Effect test

Embodiment 1

[0045] (1) 9β,10α-Dehydroprogesterone ketal photochemical deactivation reaction

[0046] Add 1L of ethyl acetate to a 3L round bottom flask, then add 30g of raw material 9α,10β-dehydroprogesterone ketal and stir to dissolve, then add 3.8mg of triethylamine and 12.5mg of 2,6-di-tert-butyl p-methyl base phenol, stirred and mixed evenly, and prepared into a photochemical reaction solution.

[0047] Into the obtained photochemical reaction solution, pass into nitrogen to protect, open the 500W high-pressure mercury lamp placed in the cold trap inner cavity in the microchannel photoreactor system I after 30 minutes, and open the cooling water valve of the system I, in the described While the cold trap is cooling down, the photochemical reaction solution is pumped into the micro-flow tube wound on the outer wall of the cold trap in system I by a peristaltic pump at a speed of 5mL / min to carry out the light reaction until the photochemical reaction solution passes through the After ...

Embodiment 2

[0054] (1) 9β,10α-Dehydroprogesterone ketal photochemical deactivation reaction

[0055] Add 1L of acetone to a 3L round bottom flask, then add 25g of raw material 9α, 10β-dehydroprogesterone ketal and stir to dissolve, then add 6.7mg of tert-butyl hydroquinone and 3.5mg of pyridine, stir and mix evenly, and prepare Photochemical reaction solution.

[0056] Into the obtained photochemical reaction solution, pass into nitrogen to protect, open the 500W high-pressure mercury lamp placed in the cold trap inner cavity in the microchannel photoreactor system I after 30 minutes, and open the cooling water valve of the system I, in the described While the cold trap is cooling down, the photochemical reaction solution is pumped into the micro-flow tube wound on the outer wall of the cold trap in the system I by a peristaltic pump at a speed of 6 mL / min to carry out the light reaction until the photochemical reaction solution passes through the After the system I is illuminated, it is...

Embodiment 3

[0063] (1) 9β,10α-Dehydroprogesterone ketal photochemical deactivation reaction

[0064] Add 300ml tetrahydrofuran to a 1L round bottom flask, then add 10g raw material 9α,10β-dehydroprogesterone ketal and stir to dissolve, then add 8.3mg 2,6-di-tert-butyl-p-cresol and 4.5mg tert-butyl Potassium alkoxide, stirred and mixed evenly, prepared into a photochemical reaction liquid.

[0065] Into the obtained photochemical reaction liquid, feed nitrogen to protect, open the 1000W high-pressure mercury lamp placed in the cold trap inner cavity in the microchannel photoreactor system 1 after 30 minutes, and open the cooling water valve of the system 1, in the described While the cold trap is cooling down, the photochemical reaction solution is pumped into the micro-flow tube wound on the outer wall of the cold trap in system I by a peristaltic pump at a speed of 5mL / min to carry out the light reaction until the photochemical reaction solution passes through the After the system I is ...

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Abstract

The invention relates to a method for synthesizing 9beta,10alpha-dehydroprogesterone ketal through photochemical isomerization in a micro-channel reactor. The method comprises the following steps: dissolving a raw material, namely 9alpha,10beta-dehydroprogesterone ketal in a medium polar solvent to prepare a solution with the concentration of 10-50 g/ml, adding an antioxidant and organic alkali into the solution, and carrying out uniform stirring and mixing to prepare a photochemical reaction solution; and introducing nitrogen is into the obtained photochemical reaction solution for protection, and conducting illumination three times so as to realize photoisomerization of 9alpha,10 beta-dehydroprogesterone ketal. According to the invention, reaction time is greatly shortened, generation ofphotoisomerization reaction by-products is inhibited, conversion rate is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a method for photochemically synthesizing 9β, 10α-dehydroprogesterone ketal with a microchannel reactor. Background technique [0002] Dehydroprogesterone is a synthetic progestin. Compared with the natural hormone progesterone, dehydroprogesterone has a trans configuration, so this type of drug is extremely stable during digestion, absorption and metabolism, and has very high oral activity. In addition, dehydroprogesterone drugs do not have the side effects of hormones such as androgen, estrogen, and corticosteroids, and are currently the most ideal progesterone drugs. Once this type of progesterone drug came out, it attracted the attention of drug researchers worldwide, and its synthesis method has also become a hot spot for chemical workers. [0003] In the synthetic route of progesterone, there are many reports on the step of photochemically synthesizing 9β, 10α-de...

Claims

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Application Information

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IPC IPC(8): B01J19/00C07J71/00
CPCB01J19/0093C07J71/0026B01J2219/00925B01J2219/00961B01J2219/00984B01J2219/00873B01J2219/00867
Inventor 陈本顺石利平叶金星徐春涛张维冰程瑞华李大伟孙伟振孟鑫何义庞小召陆梦云
Owner JIANGSU ALPHA PHARM CO LTD
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