A kind of preparation method of 16-ene steroid compound

A technology of steroidal compounds and compounds, which is applied in the production of steroidal compounds, organic chemistry, bulk chemicals, etc., can solve the problems of miscellaneous products, inability to react, low yield, etc.

Active Publication Date: 2022-08-09
TIANJIN PHARMA GROUP CORP
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  • Abstract
  • Description
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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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  • A kind of preparation method of 16-ene steroid compound
  • A kind of preparation method of 16-ene steroid compound
  • A kind of preparation method of 16-ene steroid compound

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Experimental program
Comparison scheme
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Embodiment 1

[0048]

Embodiment 1-1

[0050]Compound 1 (5 g, 13.5 mmol) was dissolved in acetonitrile (100 ml), trimethylsilyl iodide (5.8 ml, 40.5 mmol) was added, the reaction was stirred at 50°C, and the reaction progress was monitored by TLC until the reaction was complete, and Na 2 S 2 O 3 After aq (300ml, 10%w / v) terminated the reaction, the liquid was separated, 200ml of ethyl acetate was extracted and separated, the combined organic phases were distilled under reduced pressure and recrystallized from ethyl acetate / petroleum ether to obtain a white solid 2 (4.4g), 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), trimethylsilyl iodide (3.8ml, 27.0mmol) was added, the reaction was stirred at 50°C, and the reaction progress was monitored by TLC until the reaction was complete, and Na 2 S 2 O 3 After aq (300ml, 10%w / v) to terminate the reaction, 200ml of ethyl acetate was added to extract and separate the liquids. After distillation under reduced pressure, recrystallization from ethyl acetate / petroleum ether gave a white solid 2-1 (4.4g) with a purity of 99.2% , the molar yield was 92%, and after testing, a small amount of substance 2 was generated in the mother liquor.

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Abstract

The present invention provides a method for preparing a 16-ene steroid compound. The compound of formula I is used as a substrate, and trimethylhalosilane is used as a dehydrating agent. The methyl halosilane is selected from one or more of trimethylchlorosilane, trimethylbromosilane and trimethyliodosilane. The beneficial effect of the present invention is to provide a method for preparing a 16-ene steroid compound with mild reaction conditions, friendly environment, easy operation, low cost and high molar yield, using trimethylhalosilane as a dehydrating agent, which is cheap and easy to obtain, The new process of the invention has more industrial value, can effectively control side reactions, and improve the reaction yield and quality.

Description

technical field [0001] The invention belongs to the field of chemical medicine synthesis, in particular 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 reaction, the reaction conditions are severe, and a large number of flammable, explosive and highly dangerous reagents are used, such as azide method, Preparation by denitrification is prone to explosion, serious environmental pollution, and low yield, and the quality of the obtained reduced product is not ideal. Therefore, finding an ideal method for synthesizing steroids at positions 16 and 17 is the focus of the invention. [0003] In addition to the synthesis of dexamethasone, the 16- and 17-position steroids are an important intermediate for steroid drugs. The double bond has good reactivity and can be well transformed into various groups. It is pre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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