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Preparation method of key intermediate of dexamethasone and betamethasone

A technology of betamethasone and dexamethasone, which is applied in the field of preparation of intermediates, can solve problems affecting product quality and yield, and achieve the effect of high material conversion rate, high quality and high purity

Inactive Publication Date: 2017-12-01
ZHEJIANG PURUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned method can generate 2-5% organic impurity in epoxy and hydrolysis process, has influenced the quality and the yield of product, therefore, needs further improvement

Method used

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  • Preparation method of key intermediate of dexamethasone and betamethasone
  • Preparation method of key intermediate of dexamethasone and betamethasone
  • Preparation method of key intermediate of dexamethasone and betamethasone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In the embodiment of the present invention, a kind of preparation method of dexamethasone and betamethasone key intermediate, the structural formula of described dexamethasone and betamethasone key intermediate is as follows:

[0027] The specific steps are as follows:

[0028] (1) Compound I first undergoes a dehydration reaction to remove a molecule of water to obtain Compound II;

[0029] (2) Under acidic conditions, compound II is added to ethanol or triethyl orthoformate to obtain 3-ether compound III;

[0030] (3) Under the condition of strong base, methyl bromide is introduced into the solution of 3-ether compound III to obtain 16-methyl compound IV;

[0031] (4) Compound IV prepares key intermediates of dexamethasone and betamethasone by oxidative dehydrogenation in the presence of a metal catalyst; its structural formula is as follows:

[0032]

[0033] In the dehydration reaction, a dehydrating agent is required, and the dehydrating agent is selected fr...

Embodiment 2

[0040] A kind of preparation method of dexamethasone and betamethasone key intermediate, the structural formula of described dexamethasone and betamethasone key intermediate is as follows:

[0041] The specific steps are as follows:

[0042] (1) Compound I first undergoes a dehydration reaction to remove a molecule of water to obtain Compound II;

[0043] (2) Under acidic conditions, compound II is added to ethanol or triethyl orthoformate to obtain 3-ether compound III;

[0044] (3) Under the condition of strong base, methyl bromide is introduced into the solution of 3-ether compound III to obtain 16-methyl compound IV;

[0045] (4) Compound IV prepares key intermediates of dexamethasone and betamethasone by oxidative dehydrogenation in the presence of a metal catalyst; its structural formula is as follows:

[0046]

[0047]

[0048] In the dehydration reaction, a dehydrating agent is required, and the dehydrating agent is selected from phosphorus pentachloride, pho...

Embodiment 3

[0055] A kind of preparation method of dexamethasone and betamethasone key intermediate, the structural formula of described dexamethasone and betamethasone key intermediate is as follows:

[0056]

[0057] The specific steps are as follows:

[0058] (1) Compound I first undergoes a dehydration reaction to remove a molecule of water to obtain Compound II;

[0059] (2) Under acidic conditions, compound II is added to ethanol or triethyl orthoformate to obtain 3-ether compound III;

[0060] (3) Under the condition of strong base, methyl bromide is introduced into the solution of 3-ether compound III to obtain 16-methyl compound IV;

[0061] (4) Compound IV prepares key intermediates of dexamethasone and betamethasone by oxidative dehydrogenation in the presence of a metal catalyst; its structural formula is as follows:

[0062]

[0063] The dehydration reaction needs to use a dehydrating agent, and the dehydrating agent is selected from phosphorus pentachloride, phosphor...

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Abstract

The invention discloses a preparation method of a key intermediate of dexamethasone and betamethasone. The preparation method specifically comprises the following steps: (1) firstly carrying out dehydration reaction on a compound I to remove a part of water, so as to obtain a compound II; (2) carrying out addition reaction on the compound II and ethanol or triethyl orthoformate under an acidic condition, so as to obtain 3-etherate III; (3) introducing methyl bromide into a solution of 3-etherate III under a strong base condition, so as to obtain a 16-methyl compound IV; and (4) carrying out oxidative dehydrogenation on the compound IV in the presence of a metal catalyst, so as to obtain the key intermediate of dexamethasone and betamethasone. According to the preparation method, the key intermediate of dexamethasone and betamethasone is directly prepared through dehydration reaction, addition reaction, substitution reaction and dehydrogenation reaction, and a brand-new preparation process is adopted, so that the process is simple, the material conversion rate is high, the purity of the final product is high, and the high quality of the key intermediate of dexamethasone and betamethasone is guaranteed.

Description

technical field [0001] The invention relates to a method for preparing an intermediate, in particular to a method for preparing a key intermediate of dexamethasone and betamethasone. Background technique [0002] The key intermediates of the dexamethasone series and the betamethasone series are the same compound, and its structural formula is as follows: [0003] [0004] The above-mentioned key intermediate compounds can be easily prepared into dexamethasone or betamethasone through the 9-position fluorination, and a series of drugs can be prepared through a series of modifications at the 3-position, 6-position, 16-position, and 21-position. In Chinese patent CN101397319, a kind of 9,11β-epoxy steroid is prepared by generating halides in aliphatic alcohol, halogenated hydrocarbon, ketones or ether solvents, then using alkali to epoxidize and then hydrolyzing with strong base A similar method is also provided in US Pat. No. 3,725,392 to prepare 9,11β-epoxy steroids. How...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 徐润星张学忠王锦凯
Owner ZHEJIANG PURUI PHARMA
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