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Method for synthesis of 6,7-methylene sterides

A technology of methylene steroids and steroidal compounds, applied in the direction of steroids, organic chemistry, etc., can solve the problems of expensive diiodomethane, limited use, large amount of diiodomethane, etc., and achieve large-scale industrial production value, The effect of low production cost and simple operation

Inactive Publication Date: 2011-06-08
JIANGSU CHUANGUO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] But there are some defectives in the above-mentioned synthetic method, and used methyl substitution reagent diiodomethane consumption is big, and report among the US4435327, its unit consumption of this step reaction has reached 16 kilograms / kg, and diiodomethane is expensive, greatly greatly in industrial production Its use is limited, so it is an urgent and significant work to find cheap and efficient alternative reagents

Method used

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  • Method for synthesis of 6,7-methylene sterides
  • Method for synthesis of 6,7-methylene sterides
  • Method for synthesis of 6,7-methylene sterides

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Under the protection of inert gas, dissolve 5g of 3β, 5-dihydroxy-6,7-double bond-15β, 16β-methylene-5β-androst-17-one in 100ml of ethylene glycol dimethyl ether, add 25g Zn-Cu reagent, add 0.25g of iodine as an initiator, stir and heat to 40°C, add 10ml of dibromomethane dropwise, a large number of bubbles will be generated at the beginning, after the reaction is slightly relaxed, continue to add dropwise, the internal temperature rises to about 70°C, 20 The drip is over in minutes.

[0034] After dropping, keep the reaction at 70° C. for 1 hour.

[0035] Follow the reaction by TLC (developer: cyclohexane: ethyl acetate = 1:2), if there are still raw material spots, continue to add 2.5 ml of dibromomethane dropwise. After the dropwise reaction was completed, the reaction was carried out at 70° C. for 1 hour. After the reaction was followed by TLC, it was cooled to room temperature. Diatomaceous earth was used to filter, and the filter cake was washed with a small am...

Embodiment 2

[0037] Under the protection of inert gas, dissolve 5g of 3β, 5-dihydroxy-6,7-double bond-15β, 16β-methylene-5β-androst-17-one in 100ml of ethylene glycol dimethyl ether, add 25g Zn-Cu reagent, add 0.25g of iodine as an initiator, stir and heat to 40°C, add 12ml of dibromomethane dropwise, a large number of bubbles will be generated at the beginning, after the reaction is slightly moderate, continue to add dropwise, the internal temperature rises to about 70°C, 25 The drip is over in minutes.

[0038] After dropping, keep the reaction at 70° C. for 1 hour. Follow the reaction by TLC (developer: cyclohexane: ethyl acetate = 1:2), if there are still raw material spots, continue to add 2.5 ml of dibromomethane dropwise. After the dropwise reaction was completed, the reaction was carried out at 70° C. for 1 hour. Post-processing is the same as above. The product was dried to obtain 3.5 g, the yield was 67%, and the purity by HPLC was 88%.

Embodiment 3

[0040] Under the protection of inert gas, dissolve 5g of 3β, 5-dihydroxy-6,7-double bond-15β, 16β-methylene-5β-androst-17-one in 100ml of ethylene glycol dimethyl ether, add 25g Zn-Cu reagent, add 0.25g of iodine as an initiator, stir and heat to 40°C, add 8ml of dibromomethane dropwise, a large number of bubbles will be generated at the beginning, after the reaction is slightly relaxed, continue to add dropwise, the internal temperature rises to about 70°C, 15 The drip is over in minutes.

[0041] After dropping, keep the reaction at 70° C. for 1 hour. Follow the reaction by TLC (developer: cyclohexane: ethyl acetate = 1:2), if there are still raw material spots, continue to add 2 ml of dibromomethane dropwise. After the dropwise reaction was completed, the reaction was carried out at 70° C. for 1 hour. Post-processing is the same as above. After drying, 3.2 g of the product was obtained, with a yield of 61%, and a purity of 85% as detected by HPLC.

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Abstract

The invention discloses a method for synthesizing a 6, 7-methylene steroid compound, comprising the following steps that: in a solvent, a steroid compound having a 6, 7-double bond structure as shown in a formula I is in contact with dibromomethane by taking iodine as an initiator under the catalysis of Zn-Cu reagent, cyclopropyl is introduced at the 6, 7-position, then the 6, 7-methylene steroidcompound as shown in a formula II is gathered from reaction products. The method is simple in operation, the applied methylating agent, namely dibromomethane, only has a unit consumption of 7 to 10kg / kg in the step of reaction, and the price of dibromomethane is relatively low, so the method has low production costs and rather high industrialized production value.

Description

technical field [0001] The present invention relates to a method for synthesizing 6,7-methylene steroid compounds. Background technique [0002] US4435327 has described a kind of synthetic method that contains 6,7-methylene steroid compound: with the compound shown in formula VII under the catalysis of Zn-Cu reagent, use diiodomethane as methylating reagent, in its 6 , 7-double bond introduces cyclopropyl, obtains formula VIII compound, and concrete reaction formula is as follows: [0003] [0004] The compound of formula VIII is a key intermediate for synthesizing a new type of steroidal progesterone drospirenone. [0005] But there are some defectives in the above-mentioned synthetic method, and used methyl substitution reagent diiodomethane consumption is big, and report among the US4435327, its unit consumption of this step reaction has reached 16 kilograms / kg, and diiodomethane is expensive, greatly greatly in industrial production Its use is limited, so it is an u...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J53/00
Inventor 李金亮赵楠
Owner JIANGSU CHUANGUO PHARMA CO LTD
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