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Preparation method of 16-ene steroid compound

A technology for steroids and compounds, applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve the problems of long reaction time, many reaction steps, and miscellaneous products.

Active Publication Date: 2019-10-01
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The phosphorus oxychloride / pyridine method, the phosphorus oxychloride / pyridine method dehydration is relatively simple and easy, the post-treatment operation is simple, the yield is relatively high, and there are many examples, but the dehydrator is mainly α elimination, so for some β structures Elimination of unresponsive
[0011] The literature Journal of Organic Chemistry; vol.51; nb.12; (1986); p.2315–2328 describes the use of TEA, FTMP, and perchloric acid methods to form 16,17 double bonds with 16 methyl groups. The disadvantage is that the product is relatively complex, and the yield is extremely low, only 8% to 34%.
The literature Steroids; vol.66; nb.8; (2001); p.623-635 method has long reaction time, many reaction steps and low yield

Method used

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  • Preparation method of 16-ene steroid compound
  • Preparation method of 16-ene steroid compound
  • Preparation method of 16-ene steroid compound

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Experimental program
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Embodiment 1

[0048]

Embodiment 1-1

[0050]Compound 1 (5g, 13.5mmol) was dissolved in acetonitrile (100ml), trimethyl iodosilane (5.8ml, 40.5mmol) was added, and the reaction was stirred at 50°C. The reaction progress was monitored by TLC until the reaction was complete, and Na 2 S 2 o 3 aq (300ml, 10% w / v) terminated the reaction, separated the liquids, extracted the liquids with 200ml ethyl acetate, combined the organic phases and obtained the white solid 2 (4.4g) by ethyl acetate / petroleum ether recrystallization after vacuum distillation. The purity is 98.5%, and the molar yield is 92%. After testing, a small amount of substance 2-1 is formed in the mother liquor.

Embodiment 1-2

[0052] Compound 1 (5g, 13.5mmol) was dissolved in acetonitrile (100ml), trimethyl iodosilane (3.8ml, 27.0mmol) was added, and the reaction was stirred at 50°C. The reaction progress was monitored by TLC until the reaction was complete, and Na 2 S 2 o 3 aq (300ml, 10% w / v) to terminate the reaction, add 200ml ethyl acetate to extract and separate liquid, and recrystallize through ethyl acetate / petroleum ether after vacuum distillation to obtain white solid 2-1 (4.4g), purity 99.2% , the molar yield is 92%. After detection, a small amount of substance 2 is generated in the mother liquor.

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Abstract

The invention provides a preparation method of a 16-ene steroid compound. A compound shown in a formula I is used as a substrate, a trimethylhalosilane is used as a dehydrating agent, and a dehydration reaction is carried out in an aprotic reaction solvent so as to form the 16-ene steroid compound II; the trimethylhalosilane is selected from one or more of trimethylchlorosilane, trimethylbromosilane and trimethyliodosilane. The preparation method of the 16-ene steroid compound has the beneficial effects of being mild in reaction conditions, environmentally-friendly, easy to operate, low in cost and high in mole yield; the trimethylhalosilane used as the dehydrating agent is cheap and easy to obtain; the new process provided by the invention has an industrialization value, can effectively control side reactions, and improves the reaction yield and quality.

Description

technical field [0001] The invention belongs to the field of chemical medicine synthesis, and in particular relates to a preparation method of a class of steroid intermediates. Background technique [0002] The traditional method for preparing 16,17-double bond intermediates of dexamethasone series products requires three-step chemical reactions, the reaction conditions are severe, and a large amount of flammable, explosive, and dangerous reagents are used, such as the azidation method, Preparation by denitrification is prone to explosion, serious environmental pollution, low yield, and unsatisfactory quality of the obtained reduced product. Therefore, finding an ideal method for synthesizing 16,17-position stesterene is the focus of the invention. [0003] In addition to the synthesis of dexamethasone, 16, 17-position steroidene is an important intermediate of steroid drugs. The double bond has good reactivity and can be well transformed into various groups. It is prepared...

Claims

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Application Information

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IPC IPC(8): C07J13/00C07J21/00
CPCC07J13/005C07J21/00Y02P20/55
Inventor 李亚玲孙建磊
Owner TIANJIN PHARMA GROUP CORP
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