Method for preparing 9β, 10-α-dehydroprogesterone ketal by dual-wavelength microfluidic technology and dual-wavelength microfluidic photochemical reactor

A photochemical reaction and chemical reactor technology, applied in the field of organic photochemical synthesis, can solve the problems of low mass transfer and heat transfer efficiency, insufficient light, uneven photoreaction, etc.

Active Publication Date: 2015-11-11
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is a fatal defect in the traditional tank-type photochemical reactor, that is, the mass and heat transfer efficiency of the photoisomerization reaction in the tank-type photochemical reactor is low. The photoreaction solution is not illuminated enough, which leads to uneven photoreaction, and a wide variety of by-products still inevitably appear in the product at the end of the reaction

Method used

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  • Method for preparing 9β, 10-α-dehydroprogesterone ketal by dual-wavelength microfluidic technology and dual-wavelength microfluidic photochemical reactor
  • Method for preparing 9β, 10-α-dehydroprogesterone ketal by dual-wavelength microfluidic technology and dual-wavelength microfluidic photochemical reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Such as figure 1 As shown, the dual-wavelength microflow photochemical reactor for the synthesis of 9β, 10α-dehydroprogesterone ketal consists of system I and system II, and both system I and system II are an independent microflow photochemical reactor, Except for the different filter wavelengths of the cold trap, the other structures are exactly the same; they are composed of a light source 1, a cold trap 2 and a microfluidic tube 3 respectively.

[0033] The cold trap is a U-shaped interlayer container with cooling water inlet and outlet, the micro-flow tube made of quartz or high borosilicate glass is wound on the outer wall of the cold trap, and the light source It is placed in the inner cavity of the cold trap and located at the place where the micro-flow tube is wound.

[0034] The liquid outlet of the micro-fluid tube in the system I communicates with a storage tank 4 through a pipeline, and the storage tank communicates with the liquid inlet of the micro-fluid ...

Embodiment 2

[0049] The 9β, 10α-dehydroprogesterone ketal was synthesized using the dual-wavelength microflow photochemical reactor used in Example 1 for the synthesis of 9β, 10α-dehydroprogesterone ketal.

[0050] (1) 9α,10β-Dehydroprogesterone Ketal B Ring Photochemical Bond Breaking Reaction

[0051] At 30°C, add 22.5 g of 9α,10β-dehydroprogesterone ketal dissolved in 1500 mL of tetrahydrofuran into a 2000 mL round bottom flask, and then add 20 mg of 2,6-di-tert-butyl-p-methoxyphenol and 8 mg of collidine, stirred and mixed evenly, and prepared into a photochemical reaction solution;

[0052] Feed nitrogen into the prepared photochemical reaction solution, open the 1000W high-pressure mercury lamp placed in the inner cavity of the cold trap that constitutes the dual-wavelength microflow photochemical reactor system I after 30 minutes, and open the cooling water valve of the system I, While cooling the cold trap, use a peristaltic pump to pump the photochemical reaction liquid into the ...

Embodiment 3

[0060] The 9β, 10α-dehydroprogesterone ketal was synthesized using the dual-wavelength microflow photochemical reactor used in Example 1 for the synthesis of 9β, 10α-dehydroprogesterone ketal.

[0061] (1) 9α,10β-Dehydroprogesterone Ketal B Ring Photochemical Bond Breaking Reaction

[0062] At 28°C, add 10 g of 9α,10β-dehydroprogesterone ketal dissolved in 2000 mL of dioxane to a 2500 mL round bottom flask, and then add 12 mg of 2,6-di-tert-butyl-p-methyl Phenol and 4 mg of pyridine were stirred and mixed uniformly to prepare a photochemical reaction solution;

[0063] Feed nitrogen into the prepared photochemical reaction solution, open the 500W high-pressure mercury lamp placed in the inner chamber of the cold trap that constitutes the dual-wavelength microflow photochemical reactor system I after 30 minutes, and open the cooling water valve of the system I. While cooling the cold trap, use a peristaltic pump to pump the photochemical reaction liquid into the micro-flow tub...

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Abstract

The invention relates to a method for preparing 9beta,10-alphat-dehydroprogesterone ketal by using a dual-wavelength microflow technology and a dual-wavelength microflow photochemistry reactor. The method comprises the following steps: performing illumination reaction in the dual-wavelength microflow photochemistry reactor under the nitrogen protection, regulating and controlling flow velocity of photochemistry reaction liquor in a system I and a system II forming the dual-wavelength microflow photochemistry reactor by using a peristaltic pump. The conversion rate of the 9beta,10-alphat-dehydroprogesterone ketal after the illumination reaction of the system I achieves 87-92%, after the illumination reaction of the system I, in terms of the consumption of the 9beta,10-alphat-dehydroprogesterone ketal, the yield of the 9beta,10-alphat-dehydroprogesterone ketal is up to 46.3%. Compared with the traditional kettle-type photochemistry reaction, the amount of the byproduct in the photoisomerization reaction is reduced to less than 2.1% through the dual-wavelength microflow photochemistry reaction technology, and the yield of the target product 9beta,10-alphat-dehydroprogesterone ketal is greatly improved.

Description

technical field [0001] The invention belongs to the technical field of organic photochemical synthesis, in particular to a method for synthesizing 9β, 10α-dehydroprogesterone ketal by using dual-wavelength microfluidic technology, and a dual-wavelength microfluidic light for synthesizing 9β, 10α-dehydroprogesterone ketal chemical 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. [H.M.Fatemi, C.Bourgain, P.Donosol, et al. Human Reproduction Vol.22, No.5pp.1260–1263, 2007. M.H.Omar, M.K.Mashita, P.S.Lim, M.A.Jamil, Journal of Steroid Biochemistry & Mol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J21/00B01J19/08
Inventor 李超王雪松张宝文
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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