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A kind of steroid 3-keto-4-ene compound synthesis process

A technology of steroidal compound and tetramethylpiperidine, which is applied in the field of steroidal 3-keto-4-ene synthesis, can solve the problems of low yield and unfavorable environmental protection, and achieve high product yield and easy operation control , the effect of mild reaction conditions

Active Publication Date: 2019-08-27
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a lower yield and uses heavy metal chromium, which is not conducive to environmental protection

Method used

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  • A kind of steroid 3-keto-4-ene compound synthesis process
  • A kind of steroid 3-keto-4-ene compound synthesis process
  • A kind of steroid 3-keto-4-ene compound synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054]

Embodiment 1-1

[0056] Add 1.11Kg of starting material, 100g ferric nitrate, 50g tempo, and 20L acetonitrile into the reaction tank, heat to reflux, keep the temperature for 16 hours until the reaction is complete as monitored by TLC, concentrate until a small amount of acetonitrile is poured into 1L, drop to room temperature, dilute in ice water, filter The discharge was dried to obtain 2.11Kg of the target product, the content was 95%, and the yield was 100%.

[0057] Embodiment 1-2~Example 1-19 operation steps and solvent reference example 1-1, and the feeding amount (unit: mole number) of initiator, transition metal catalyst, piperidine class nitroxide free radical catalyst and implementation Example 1-1 is the same. Embodiment 1-2~Example 1-15 air oxidation. Embodiment 1-16~Example 1-19 feed oxygen.

[0058]

[0059]

Embodiment 2

[0061]

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Abstract

The invention discloses a new process for synthesizing steroid 3-one-4-ene. The method comprises the steps: with steroid 3-hydroxy-5-ene as a starting material, in a nonprotic organic solvent, with air or oxygen as an oxidant and with a transition metal nitrate and a 2,2,6,6-tetramethylpiperidine-1-oxyl free radical or an analogue thereof as catalysts, oxidizing to obtain the steroid 3-one-4-ene. The method has the advantages of high yield, mild reaction conditions, easily controlled operation, low energy consumption, low cost, and safety; and the whole process is friendly to the environment, and is suitable for industrialization.

Description

[0001] Technical field: [0002] The invention relates to a new process for the synthesis of steroid 3-keto-4-ene. [0003] Background technique: [0004] The preparation of 3-keto-4-ene steroids by oxidation of 3β-hydroxy-5-ene steroids plays an important role in the synthesis of steroids, such as the important intermediate of corticosteroids Woshi oxide (16,17α-epoxy -4-pregnene-3,20-dione) is obtained by oxidation of 16,17α-epoxy-3-hydroxypregnene-5-en-20-one. At present, this type of reaction is mainly prepared by the Oppenauer oxidation method in industry, that is, toluene is used as the solvent, and aluminum isopropoxide-cyclohexanone is used as the reaction reagent. This method consumes a lot of energy. On the one hand, the reaction needs to be reacted under reflux. On the other hand, after the reaction is completed, the solvent must be evaporated by concentrating under reduced pressure. The boiling point is very high, so the whole reaction process consumes a lot of en...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J75/00C07J71/00C07J13/00C07J1/00C07J7/00C07J5/00
Inventor 李亚玲王淑丽
Owner TIANJIN JINYAO GRP