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A method for synthesizing 7a-methyl formate-9(11)-encanrenone

A technology of encanrenone and methyl formate, which is applied in the field of medicine and chemical industry, can solve the problems of high toxicity and unsuitability for industrial production, achieve the effects of less pollution of three wastes, simplify redox re-oxidation and esterification operations, and reduce production costs

Active Publication Date: 2021-01-01
YANGZHOU LIANAO BIOMEDICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The route uses 9(11)-encanrenone as a raw material, uses hydrocyanic acid as a cyanide source to place a cyano group on the 7-position of the steroidal ring, and then uses diisobutylaluminum hydride (DIBAL) to hydrolyze the cyano group into a formaldehyde group, and then Esterification after oxidation with chromium trioxide to obtain 7a-methyl formate-9(11)-encanrenone, reagents such as highly toxic hydrocyanic acid and flammable and explosive diisobutyl aluminum hydride in this route, do not Suitable for industrial production

Method used

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  • A method for synthesizing 7a-methyl formate-9(11)-encanrenone
  • A method for synthesizing 7a-methyl formate-9(11)-encanrenone
  • A method for synthesizing 7a-methyl formate-9(11)-encanrenone

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Experimental program
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Effect test

Embodiment 1

[0024]

[0025] Add 20 g (0.0591 mol, 1.0 equiv) of 9(11)-encanrenone, 100 mL of acetonitrile, and 9.12 g (0.111 mol, 1.88 equiv) of 2-methylfuran into the reactor under nitrogen protection, and cool down to -20 ~-25°C, add 12.16g (0.0857 mol, 0.45 equiv) of boron trifluoride diethyl ether solution dropwise, after dropping, keep warm for 4 hours, TLC detection to control the reaction end point, after the reaction is completed, add 10 mL of triethylamine (0.0719 mol, 1.22 equiv) to stop the reaction, concentrate to dryness under reduced pressure, add 200 mL of dichloromethane and 100 mL of water, wash and separate layers, concentrate the organic layer to dryness under reduced pressure, recrystallize with methyl tert-butyl ether, filter, and dry to obtain white The solid 7a-(5-methyl-2furan)-9(11)-encanrenone was 18.2 g, the molar yield was 73.23%, and the HPLC purity was 98.92%.

[0026]

[0027] Add 20g (0.0476 mol, 1.0 equiv) of 7a-(5-methyl-2-furan)-9(11)-encanrenone, ...

Embodiment 2

[0032]

[0033] Add 20g of 7a-(1,4-dicarbonylpentene)-9(11)-encanrenone (0.0458mol, 1.0equiv), 200mL of methanol, and 200ml of dichloromethane to the reactor under nitrogen protection, and cool down To about -50°C, react with ozone, TLC to determine the end point of the reaction, the reaction is complete, replace with nitrogen, heat up to 0°C, add 30g of iron powder for reduction, test the non-oxidative properties of starch potassium iodide test paper, filter, and concentrate the filtrate under reduced pressure until a large amount of solids precipitate , put on a silica gel column, collect the chromatographic solution and concentrate to dryness to obtain 7.2 g of the target product, with a molar yield of 39.45% and an HPLC purity of 98.56%.

Embodiment 3

[0035]

[0036] Add 20g of 7a-(1,4-dicarbonylpentene)-9(11)-encanrenone (0.0458mol, 1.0equiv), 200mL of methanol, 200ml of toluene to the reaction kettle under the protection of nitrogen, and cool down to - At about 50°C, react with ozone, TLC determines the reaction end point, the reaction is complete, replace with nitrogen, keep warm to -50°C, add 2g of magnesium powder for reduction, test the non-oxidative properties of starch potassium iodide test paper, filter, and concentrate the filtrate under reduced pressure until a large amount of solids are precipitated. Put on a silica gel column, collect the chromatographic solution and concentrate to dryness to obtain 6.8 g of the target product, with a molar yield of 37.25% and an HPLC purity of 98.44%.

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Abstract

The invention discloses a method for synthesizing 7a-methyl formate-9(11)-encanrenone. The method comprises the following steps: reacting 9(11)-encanrenone used as a raw material with 2-methylfuran atfirst, performing ring opening by using dibromohydantoin, rearranging, ozonizing, adding a metal reducing agent to methanol or a mixed solution of methanol and other solvent, and performing reducingesterification to directly obtain the 7a-methyl formate-9(11)-encanrenone. The method has the advantages of operation step simplification, high yield, simplicity in operation, few three wastes, and suitableness for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 7a-methyl formate-9(11)-encanrenone, which belongs to the technical field of medicine and chemical industry. Background technique [0002] Eplerenone (EPL) was approved by the US FDA on September 27, 2002 as a new molecular entity, and was first listed in the United States on January 31, 2004, under the trade name Inspra; it is a new type of selective aldosterone receptor Antibody antagonists block the effect of aldosterone in the renin-angiotensin-aldosterone system (RAAS) with aldosterone receptors, thereby reducing blood pressure. In 2003, the US FDA approved eplerenone for treatment A new indication for congestive heart failure after acute myocardial infarction, clinical studies have confirmed that eplerenone is effective in improving left ventricular systolic dysfunction after acute myocardial infarction (ejection fraction ≤ 40%) and stable patients with clinical evidence of congestive heart failu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J21/00C07J71/00
CPCC07J21/003C07J71/0015
Inventor 姜倩倩许峰洪香仙谢晓强陈文娇庞绍峰
Owner YANGZHOU LIANAO BIOMEDICAL CO LTD
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