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Chemical synthesis method of 5,7-diene steroids compounds

A technology of diene steroids and a synthesis method, which is applied in 5 fields, can solve the problems of affecting the photochemical reaction of vitamin D drugs, serious pollution, high price and the like, and achieves low production cost, high reaction yield and mild reaction conditions. Effect

Active Publication Date: 2009-03-11
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Before the present invention was made, most of the chemical synthesis methods of prior art 5,7-diene steroids used 5-ene-7-bromo steroids as raw materials to obtain 5,7-diene steroids through debromination, For example in Bu 4 N + F-, debromination in systems such as collidine (WO2008089093, US2571330) to obtain 5,7-diene steroids, the yield of this method is low, about 30-50%, and the pollution is serious
5,7-diene steroids can also be obtained from 7-sulfoxide substituents through elimination reactions (J.Org.Chem., 1981, 46, 1030; Tetrahedron Lett., 1991, 32, 5171; US20080171728) The yield is medium; it can also be obtained from the 7-ester substituent by noble metal Pd catalysis or high-temperature elimination reaction by heating (Tetrahedron Lett., 1992, 33, 2549; J.Am.Chem.Soc., 1952, 74, 3318), This method uses the expensive Pd catalyst, the cost is higher
In addition, the above method will also produce some impurities that cannot be removed, which will seriously affect the photochemical reaction in the synthesis of vitamin D drugs.

Method used

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  • Chemical synthesis method of 5,7-diene steroids compounds
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  • Chemical synthesis method of 5,7-diene steroids compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0028] In a 1000ml four-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 100mmol (61g) of 3-acetoxycholesterol-7-p-toluenesulfonylhydrazone, dissolve it in 400mL of toluene, cool to -20°C, add A solution of methyl lithium (6.6 g, 300 mmol) in toluene (50 mL) was maintained at -20°C, reacted for 0.5 hour, then raised to 25°C and stirred for 2 hours. After the reaction is complete, add 100 mL of water and stir thoroughly, add 4 g of sodium hydroxide, heat up to reflux, react for 30 minutes, adjust the pH to 7 with hydrochloric acid or acetic acid, leave the organic phase to dry with anhydrous sodium sulfate after standing for layers, and evaporate the solvent. Recrystallization with ethanol / toluene gave 36.1 g of the target product 5,7-dienyl cholesterol as a light yellow solid with a melting point of 145-146° C. and a yield of 94%.

Embodiment 2

[0030] In a 1000ml four-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 100mmol (61g) of 3-acetoxycholesterol-7-p-toluenesulfonylhydrazone, dissolve it in 400mL of toluene, cool to -20°C, add A solution of methyl lithium (6.6 g, 300 mmol) in toluene (50 mL) was maintained at -20°C, reacted for 0.5 hour, then raised to 25°C and stirred for 2 hours. After the reaction is complete, add 100 mL of methanol and stir thoroughly, add 4 g of sodium hydroxide, heat up to reflux, react for 30 minutes, adjust the pH to 7 with hydrochloric acid or acetic acid, evaporate the solvent, and recrystallize with ethanol / toluene to obtain the target product 5,7- 36.6 g of Diene Cholesterol is a light yellow solid with a melting point of 145-146° C. and a yield of 95%.

Embodiment 3

[0032] In a 1000ml four-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 100mmol (61g) of 3-acetoxycholesterol-7-p-toluenesulfonylhydrazone, dissolve it in 400mL of toluene, cool to -20°C, add A solution of methyl lithium (6.6 g, 300 mmol) in toluene (50 mL) was maintained at -20°C, reacted for 0.5 hour, then raised to 25°C and stirred for 2 hours. After the reaction is complete, add 100 mL of ethanol and stir thoroughly, add 4 g of sodium hydroxide, heat up to reflux, react for 30 minutes, adjust the pH to 7 with hydrochloric acid or acetic acid, evaporate the solvent, and recrystallize with ethanol / toluene to obtain the target product 5,7- 36.6 g of Diene Cholesterol is a light yellow solid with a melting point of 145-146° C. and a yield of 95%.

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Abstract

The invention discloses a method for synthesizing a 5, 7-diene steroidal compound as shown in a formula (I), which comprises the following steps of allowing a hydrazone as shown in a formula (II) to react with an alkali as shown in a formula (III) in an organic solvent for 0 to 6 hours at the temperature of between minus 20 and 50 DEG C, then heating to 25 and 150 DEG C, preserving the temperature to react for 0.5 to 6 hours, de-protecting the reaction solution, recycling the solvent to obtain a crude product, and recystallizing the crude product to obtain the finished product 5, 7-diene steroidal compound. The method has mild reaction conditions, high reaction yield (generally more than 85 percent, and even more than 95 percent), low production cost and good selectivity, and therefore is an advanced technique route.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 5,7-diene steroids. (2) Background technology [0002] 5,7-diene steroids are the precursors of vitamin D drugs, which are widely used in medicine, food, pesticide, chemical industry and other fields, and have high practical value. The main function of vitamin D drugs is to regulate the metabolism of calcium and phosphorus, promote the absorption of calcium and phosphorus in the intestine and bone calcification, and maintain the balance of blood calcium and blood phosphorus. Essential vitamins for good health. [0003] Before the present invention was made, most of the chemical synthesis methods of prior art 5,7-diene steroids used 5-ene-7-bromo steroids as raw materials to obtain 5,7-diene steroids through debromination, For example in Bu 4 N + F-, collidine (WO2008089093, US2571330) and other systems are debrominated to obtain 5,7-diene steroids. The yield of this method is low, about 30...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 金灿苏为科闻光东王子强马焕政
Owner ZHEJIANG UNIV OF TECH
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