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Synthetic method for eplerenone

A synthesis method and technology of eplerenone, applied in the direction of steroids, organic chemistry, etc., can solve problems such as lack of large-scale synthesis advantages

Inactive Publication Date: 2006-03-22
NANJING UNIV
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  • Description
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  • Application Information

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Problems solved by technology

Directly lead to the above route does not have obvious large-scale synthesis advantages

Method used

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  • Synthetic method for eplerenone
  • Synthetic method for eplerenone
  • Synthetic method for eplerenone

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Experimental program
Comparison scheme
Effect test

Embodiment

[0022] Embodiment: As above-mentioned experimental procedure: Under the situation that substrate 11α-curry ketone, acetone cyanohydrin and solvent consumption are the same, use other quaternary ammonium bases such as 130.0mL25% tetraethylammonium hydroxide aqueous solution, 180.0mL25% tetrapropylhydrogen Ammonium oxide, 228.0mL 25% tetrabutylammonium hydroxide or 147.0mL 25% benzyltrimethylammonium hydroxide had no significant effect on the yield of enamine 8, but the amount of quaternary ammonium bases with different structures changed.

[0023] Embodiment: Adopt propanol, isopropanol or butanol and ethanol solvent to have no obvious difference, but reflux temperature is different, and reaction time is 0.5 hour productive rate is low, and the time is long to 10 hours efficiency low; Reaction temperature has no obvious requirement, can be in The reaction is at room temperature, and the temperature does not exceed 70-100°C of the reflux temperature of the solvent when the temper...

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Abstract

The synthesis process of eplerenone includes the following steps: double serial Michael addition / Aldo condensation reaction of 11alpha-hydroxyl curry ketone and acetone cyanohydrin to produce enamine, partially hydrolyzing the enamine to produce intermediate compound, opening ring of the intermediate compound to obtain the compound IX; eliminating reaction produced olefine ester from the compound IX, reaction with phosphorous oxychloride at room temperature for 12-24 hr, extracting with methane dichloride solvent, merging organic phase, washing and drying to obtain compound X; performing 9alpha, 11-double bond selective expoxidation, extracting the water layer with methane dichloride and merging the organic phase; washing with NaHSO3 solution, saturated Na2SO3 solution, dilute hydrochloric acid solution and saturated hydrochloric acid solution successively, drying, distillation at normal pressure and concentration to obtain eplerenone.

Description

1. Technical field [0001] The invention relates to a new method for synthesizing eplerenone, in particular to synthesizing eplerenone from 11α-hydroxy curry ketone through multi-step chemical reactions. 2. Background technology [0002] Aldosterone (1) is a natural corticosteroid whose secretion is controlled by the renin-angiotensin system and the concentration of potassium ions in the serum. Aldosterone can promote the absorption of sodium ions and the excretion of potassium ions, and regulate the composition of electrolytes in the body. However, the presence of too much aldosterone can lead to cardiovascular diseases such as myocardial fibrosis, left ventricular hypertrophy, congestive heart failure and essential hypertension. Studies have found that the pathophysiological mechanism of aldosterone is mainly through direct binding to mineralocorticoid receptors in epithelial tissues (such as kidney) and non-epithelial tissues (such as heart, blood vessels and brain). The...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 王少仲李建新王磊杜云黄乐群
Owner NANJING UNIV
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