Synthesis method of single optical isomer nitrendipine

A synthesis method, photoisomerization technology, applied in the direction of organic chemistry, etc.

Inactive Publication Date: 2005-08-10
JIAXING UNIV
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Problems solved by technology

Synthesized in the above-mentioned documents are all racemic nitrendipine, and the method for chiral catalytic synthesis of optically active single isomer nitrendipine has not been reported

Method used

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  • Synthesis method of single optical isomer nitrendipine
  • Synthesis method of single optical isomer nitrendipine
  • Synthesis method of single optical isomer nitrendipine

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Embodiment Construction

[0008] The synthesis method of this single optical isomer nitrendipine is as follows: using absolute ethanol as a solvent, 2-(3-nitro)benzylidene acetoacetate and β-aminocrotonic acid methyl ester are in the chiral phase. In the presence of the transfer catalyst quinine benzyl ammonium bromide, a stereoselective condensation reaction is performed to obtain the product.

[0009] The reaction formula is as follows:

[0010]

[0011] The specific synthesis example is: add 20ml of absolute ethanol, 13.2g (0.05mol) of ethyl 2-(3-nitrobenzylidene)acetoacetate (II), methyl β-aminocrotonate ( I) 5.75g (0.05mol), 0.13g of quinine benzylammonium bromide (IV), stirred and refluxed for reaction, the temperature was controlled at 78°C, and the reaction time was 4 hours. After the reaction, the reaction solution was distilled under reduced pressure to evaporate part of the ethanol. The reaction solution was frozen for 3 hours and filtered with suction to obtain yellow crystals, which were rec...

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Abstract

A process for synthesizing the simple optical isomer nitrendipine features that under existance of quinine-ammonium benzylbromide as chiral phase-transfer catalyst, 2-(3-nitrobenzilidene) ethyl acetylacetate and beta-methyl amino crotonate take part in stereoselective condensating reaction in absolute alcohol to obtain target product.

Description

Technical field [0001] The invention relates to 2,6-dimethyl-4-(3-nitro)phenyl-1,4-dihydropyridine-3-carboxylic acid ethyl ester-5-methyl formate (referred to as Nitrendipine) Synthetic method, a synthetic method of a single optical isomer nitrendipine. Background technique [0002] 2,6-Dimethyl-4-(3-nitro)phenyl-1,4-dihydropyridine-3-carboxylic acid ethyl ester-5-carboxylic acid methyl ester (nitrendipine), also known as "nitrendipine" (hereinafter Abbreviated as Nitrendipine), is a dihydropyridine calcium antagonist, clinically mainly used for the treatment of primary and secondary hypertension, but also has the effect of treating other cardiovascular diseases. The appearance is bright yellow crystal or crystalline powder. The structure of Nitrendipine means that it contains a chiral carbon and there are two enantiomers. For chiral drugs, there have been many reports on other examples where the physiological activities of the two isomers are significantly different. Single chir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/90
Inventor 吴建一
Owner JIAXING UNIV
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