Synthesis of 16α,17α-epoxy-4-pregnene-3,20-dione

A synthetic method, the technology of pregnene, applied in the direction of steroids, organic chemistry, etc., can solve the problems of low yield, high production cost, environmental pollution of toluene vapor, etc., to reduce environmental pollution, reduce production cost, and reduce temperature Effect

Inactive Publication Date: 2011-12-21
SHAANXI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In summary, the prior art has the disadvantages of large amount of solvent, oxidant and catalyst, high producti

Method used

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  • Synthesis of 16α,17α-epoxy-4-pregnene-3,20-dione

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0023] Put 2kg of oxygen bridge into the flask, then add 22L of n-heptane and 8L of cyclohexanone, install a thermometer and a water separator on the flask, heat and stir with water. When there are no drops of water in the water separator, cool down to ≤90°C, add 0.32kg aluminum isopropoxide, cool down to ≤90°C after intense reflux for 4 hours, add dropwise 0.3kgNaOH and 1LH 2 O prepared alkaline water. After the dropwise addition was completed, stir and reflux for 20 minutes, and then remove the lower alkaline water. Then add 0.08kgNaOH and 4.4LH 2 O prepared alkaline water was stirred and refluxed for 30 minutes, and the lower alkaline water was separated. Finally, add 0.044kgNaOH and 4.4LlH 2 The alkaline water prepared by O is distilled at atmospheric pressure to oil-free beads (an appropriate amount of boiling water needs to be added during the distillation). Suction filtration, washing filter cake to neutral. After the filter cake was dried, 1.9 kg of crude product ...

Embodiment 2

[0025] Put 5kg of oxygen bridge into the flask, then add 55L of n-heptane and 20L of cyclohexanone, install a thermometer and a water separator on the flask, heat and stir with water. When there are no drops of water in the water separator, cool down to ≤90°C, add 0.8kg aluminum isopropoxide, cool down to ≤90°C after vigorously refluxing for 4 hours, add dropwise 0.75kgNaOH and 2.5LH 2 O prepared alkaline water. After the dropwise addition was completed, stir and reflux for 20 minutes, and then remove the lower alkaline water. Then add 0.2kgNaOH and 11LH 2 O prepared alkaline water was stirred and refluxed for 30 minutes, and the lower alkaline water was separated. Finally, add 0.11kgNaOH and 11LlH 2 The alkaline water prepared by O is distilled at atmospheric pressure to oil-free beads (an appropriate amount of boiling water needs to be added during the distillation). Suction filtration, washing filter cake to neutral. After the filter cake was dried, 4.76kg of the crude...

Embodiment 3

[0027] Put 8 kg of oxygen bridge into the flask, then add 88 L of n-heptane and 32 L of cyclohexanone, install a thermometer and a water separator on the flask, heat and stir with water. When there are no drops of water in the water separator, cool down to ≤90°C, add 1.28kg of aluminum isopropoxide, cool down to ≤90°C after intense reflux for 4 hours, add dropwise 1.2kgNaOH and 4LH 2 O prepared alkaline water. After the dropwise addition was completed, stir and reflux for 20 minutes, and then remove the lower alkaline water. Then add 0.32kgNaOH and 17.6LH 2 O prepared alkaline water was stirred and refluxed for 30 minutes, and the lower alkaline water was separated. Finally, add 0.176kgNaOH and 17.6LlH 2 The alkaline water prepared by O is distilled at atmospheric pressure to oil-free beads (an appropriate amount of boiling water needs to be added during the distillation). Suction filtration, washing filter cake to neutral. After the filter cake was dried, 7.7 g of crude ...

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Abstract

The invention discloses a synthesis method of 16α, 17α-epoxy-4-pregnene-3, 20-dione. The process steps are: 10.0 parts of oxygen bridge, 70-80 parts of n-heptane and 35-40 parts of Mix 6-7 parts of cyclohexanone, heat and stir with water; after cooling down, add aluminum isopropoxide catalyst, reflux vigorously for 4 hours, cool down; add 6-7 parts of 30% NaOH solution dropwise, reflux for 20 minutes, add 2 % NaOH solution 20-25 parts, reflux for 30min, and remove alkaline water; then add 1% NaOH solution 20-25 parts, distill until no oil drops, suction filter, wash, dry; then dissolve with absolute ethanol, Reflux, freezing, suction filtration, Dewas oxide. The consumption of solvent, oxidant and catalyst of the present invention is less, only needs twice alkali washing, has simplified technology, has reduced production cost, and the content of Wo Shi oxidation reactant can reach 98.2%, and productive rate is more than 80%; The use of toluene reduces environmental pollution.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to an improvement to a synthesis method of 16α, 17α-epoxy-4-pregnene-3,20-dione. Background technique [0002] 16α, 17α-epoxy-4-pregnene-3, 20-dione, also known as 16α, 17α-epoxy progesterone, referred to as Woshi oxide, English name: 16α, 17α-epoxyprogesterone, is a synthetic steroid corticosteroid The extremely important intermediate of hormone and steroidal progesterone is 3β-hydroxy-pregna-5,16-diene-20-one-3-acetate (referred to as diene), which is oxidized by hydrogen peroxide to obtain 3β-hydroxy- 16,17α-epoxy-pregnant-5-en-20-one (referred to as oxygen bridge), and then generated by Woshi oxidation. Most of the solvents for the synthesis of Woshi oxide are prepared with toluene and cyclohexanone or benzene and acetone. There are also reports of cyclohexane, xylene or dioxane as solvents. Domestic and foreign literature reports generally use the solv...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 田光辉刘存芳王顺民赖普辉赵桦蒋翔聂峰孙志锋
Owner SHAANXI UNIV OF TECH
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