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Preparation method of 5 alpha-androstane-2-ethylene-17-ketone

A technology of androsterone and epiandrosterone, which is applied in the field of chemical preparation, can solve the problems of complicated operation, low atom economy, large amount of three wastes, etc., and achieves the effects of shortening reaction steps, simple post-processing and reducing discharge amount.

Inactive Publication Date: 2019-04-26
台州仙琚药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to solve the problem that the current preparation method of 5α-androst-2-en-17-one uses a large amount of organic base, low atom economy, poor reaction selectivity and cumbersome operation, which lead to related methods that cannot be industrialized or are in the process of industrialization. The cost is too high in the process, and the technical problems of the three wastes are too large

Method used

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  • Preparation method of 5 alpha-androstane-2-ethylene-17-ketone

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Experimental program
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Effect test

Embodiment 1

[0022] Add epiandrosterone (10mmol, 2.9g), p-toluenesulfonic acid (2mmol, 0.34g) and ytterbium trifluoromethanesulfonate (0.5mmol, 310mg) into a 50mL single-port reaction flask, toluene (20mL) as a solvent, 110°C Reaction 16h. After cooling the reaction solution to room temperature, pour it into 100mL of ice water, add 50mL of dichloromethane for extraction, wash the organic layer with saturated sodium bicarbonate solution and dry (anhydrous sodium sulfate), then distill and concentrate under reduced pressure to obtain a dark brown oil , the residue was recrystallized by 80% aqueous ethanol to obtain 2.4 g of 5α-androst-2-en-17-one, with a yield of 88%.

[0023] After testing, the specific characteristics of the product are as follows:

[0024] Melting point: 108.2-110.1℃, 1 H NMR (400MHz, CDCl 3 )δ5.67-5.55(m,2H),2.46(dd,J 1 =6.0Hz,J 2 =12.8Hz,1H),2.12-2.06(m,1H),1.99-1.88(m,2H),1.86-1.80(m,2H),1.78-1.70(m,2H),1.68-1.59(m,2H ),1.57-1.50(m,3H),1.46-1.40(m,2H),1.32-1.25(m...

Embodiment 2

[0026] According to the method and steps of Example 1, the only difference is that the molar ratio of epiandrosterone and p-toluenesulfonic acid was adjusted to 1:0.1, the reaction time was adjusted to 18 hours, and the yield was 78%.

Embodiment 3

[0028] According to the method and steps of Example 1, the only difference is that the molar ratio of epiandrosterone and ytterbium trifluoromethanesulfonate was adjusted to 1:0.1, the reaction time was adjusted to 8 hours, and the yield was 85%.

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Abstract

The invention discloses a preparation method of 5 alpha-androstane-2-ethylene-17-ketone. The preparation method comprises the steps of taking epiandrosterone (formula I as shown in the specification)as a raw material to give a dehydration reaction by joint catalysis of protonic acid and trifluoromethanesulfonate, and performing post-treatment, recrystallization and separation on a reaction product to form 5 alpha-androstane-2-ethylene-17-ketone (formula II as shown in the specification). The preparation method avoids the use of much organic base compound in the traditional method, has the advantages of high reaction yield, short procedure, good selectivity, low cost, less waste gas, waste water and industrial residue and the like and is a synthesis method suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of chemicals, in particular to a preparation method of 5α-androst-2-en-17-one. Background technique [0002] 5α-androst-2-en-17-one is an important intermediate for the synthesis of muscle relaxants such as rocuronium bromide, vecuronium bromide and pancuronium bromide. Sterol ammonium bromide drugs, including rocuronium bromide and vecuronium bromide, are a new type of non-depolarizing muscle relaxants that have emerged in recent years. It has clinical advantages such as weak effect and small release of histamine, and has become an effective new anesthetic substitute for succinylcholine. [0003] Since 5α-androst-2-en-17-one is a common intermediate in the synthesis of this type of sterol muscle relaxant, it is of great practical significance to study its simple and efficient industrial preparation method. The existing commonly used method for preparing 5α-androst-2-en-17-one is generally divided into tw...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 金炜华潘建洪顾光志
Owner 台州仙琚药业有限公司
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