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Preparation method and application of 1alpha-dehydroepiandrosterone

A technology for dehydroepiandrosterone and epiandrosterone, which is applied in the directions of steroids, organic chemistry, etc., can solve the problems of long production cycle, high production cost, complicated process, etc., and achieves low production cost, short production cycle, and high technology. Simple process effect

Active Publication Date: 2010-09-29
REYOUNG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The 1α-hydroxydehydroepiandrosterone in the prior art is prepared by microbial fermentation method, which has complex process, long production cycle, low yield and high production cost

Method used

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  • Preparation method and application of 1alpha-dehydroepiandrosterone
  • Preparation method and application of 1alpha-dehydroepiandrosterone
  • Preparation method and application of 1alpha-dehydroepiandrosterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 1α-hydroxy dehydroepiandrosterone according to the preparation method of the present invention

[0029] a. Dehydrogenation and oxidation to prepare intermediate compound II:

[0030] Dissolve 56.5 g of allyl diethyl phosphate and 750 mg of palladium acetate in 100 ml of dimethylformamide, stir at room temperature for 30 min, add 14.5 g of ethylene glycol dehydroepiandrosterone, 37.0 g of sodium carbonate, and , Stirring and reflux for 8h. After adding 10% citric acid, extraction was performed with dichloromethane. After concentration, it was recrystallized with methanol to obtain 12.1 g of intermediate compound II, namely 17,17-ethylenedioxy-1,4,6-triene-androst-3-one, with a yield of 85.0%.

[0031] Melting point: 130~132℃, [α] D : -39 (c=0.55, methanol). 1H-NMR (600MHZ, CDCl 3 )δ: 7.07 (1H, d, J = 10.2Hz), 6.22-6.26 (2H, m), 6.05 (1H, dd, J = 10.2, 1.8Hz), 6.03 (1H, s), 3.82-3.90 (4H , m), 2.28 (1H, t, J=10.2Hz), 2.04 (1H, m), 1.82-1.87 (3H, m), 1...

Embodiment 2

[0041] According to the method and steps of Example 1, the only difference is that the same reaction is carried out with dimethyl allyl phosphate instead of diethyl allyl phosphate, and the yield of step a is 78.6%.

Embodiment 3

[0043]According to the method and steps of Example 1, the only difference is that potassium carbonate is used instead of sodium carbonate to carry out the same reaction, and the yield of step a is 71.6%.

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Abstract

The invention relates to a preparation method of 1alpha-dehydroepiandrosterone, belonging to a preparation method of steroide compounds. The preparation method is characterized by comprising the following steps of: carrying out a dehydrogenated oxidizing reaction on glycol-condensed dehydroepiandrosterone as a raw material under the action of a metallic palladium catalyst, an allyl phosphodiester ligand and alkali to generate conjugated ketene; and carrying out epoxidation and liquid ammonia-metal reduction and deprotecting reaction to obtain the 1alpha-dehydroepiandrosterone. The invention has the advantages of simple process flow, short production cycle, high product yield, low production cost, low price and easy accessibility of the raw material and a reagent, simple operation, no need of column chromatography and other operations and suitability for large-scale preparation and production. In addition, the invention solves the problems of complicated process, long production cycle, low yield and high production cost existing in the method for fermenting microorganisms in the prior art.

Description

technical field [0001] The invention is a preparation method of 1α-hydroxy dehydroepiandrosterone. It belongs to the preparation method of steroid compounds. Background technique [0002] 1,25-Dihydroxyvitamin D 3 is vitamin D 3 The active form that plays a physiological role, in addition to the function of regulating calcium and phosphorus metabolism in the body, active vitamin D 3 And its derivatives are also excellent differentiation inducers and proliferation inhibitors, immunomodulators, etc., and are commonly used clinically to treat osteoporosis, renal insufficiency, hyperparathyroidism, psoriasis skin hyperplasia, cancer, diabetes , immune diseases, etc. 1α-Hydroxydehydroepiandrosterone is the synthetically active vitamin D 3 Key intermediates of drugs. [0003] The 1α-hydroxydehydroepiandrosterone in the prior art is prepared by microbial fermentation, which has complicated process, long production cycle, low yield and high production cost. Contents of the i...

Claims

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Application Information

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IPC IPC(8): C07J1/00C07C401/00
Inventor 刘兆鹏尹贻贞刘超娄红祥李广
Owner REYOUNG PHARMA
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