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7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-alpha]imidazole-5(6H)-ketone and synthetic method thereof

The technology of a difluoromethyl group and a synthesis method, which is applied in the field of 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-5(6H)-one and its synthesis, can Solve the problems that have not been reported, and achieve the effects of high fat solubility and hydrophobicity, better physiological activity, and stable product structure

Inactive Publication Date: 2009-08-26
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The synthesis method of this compound has not been reported yet

Method used

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  • 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-alpha]imidazole-5(6H)-ketone and synthetic method thereof
  • 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-alpha]imidazole-5(6H)-ketone and synthetic method thereof
  • 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-alpha]imidazole-5(6H)-ketone and synthetic method thereof

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Embodiment 1

[0030] Embodiment 1: The following steps are adopted for the preparation of 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-5(6H)-ketone: 1. in a 50 ml reflux condenser Add 0.40 g of ethyl difluoroγ-ketoate, 0.019 g of p-toluenesulfonic acid, 25 ml of toluene, and 0.2 g of anhydrous magnesium sulfate into a round bottom flask. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 0.12 g of 1,2-ethylenediamine was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 0.019 g of p-toluenesulfonic acid was added. The reaction was continued for 12 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrate was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 to obtain 0.31 g of a yellow liquid w...

Embodiment 2

[0031] Embodiment 2: Preparation of 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-5(6H)-ketone adopts the following steps: 1. in a 250 ml reflux condenser Add 10 grams of ethyl difluoroγ-ketoate, 0.475 grams of p-toluenesulfonic acid, 150 milliliters of toluene, and 5 grams of anhydrous magnesium sulfate into the round bottom flask. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 3.0 g of 1,2-ethylenediamine was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 0.475 g of p-toluenesulfonic acid was added. The reaction was continued for 16 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrated solution was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 to obtain 7.21 g of ...

Embodiment 3

[0032] Embodiment three: the following steps are adopted for the preparation of 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-5(6H)-ketone: 1. in a 2-liter reflux condenser Add 100 grams of ethyl difluoroγ-ketoate, 4.75 grams of p-toluenesulfonic acid, 1000 milliliters of toluene, and 25 grams of anhydrous magnesium sulfate into the round bottom flask. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 30 g of 1,2-ethylenediamine was added. ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 4.75 g of p-toluenesulfonic acid was added. The reaction was continued for 24 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrated solution was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 to...

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Abstract

The invention relates to 7a-(difluoromethyl) tetrahydro-1H-pyrrolo [1,2-alpha]imidazole-5(6H)-ketone and a synthetic method thereof. The structural formula can be seen in the diagram, and the method comprises the following steps: dissolving p-toluenesulfonic acid based on the usage of difluoro Gamma- ketone acid methyl ester and catalyst in the toluene, adding anhydrous magnesium sulfate based on the usage of catalyst to reflux for 20-60 minutes while stirring, then adding 1,2-ethylenediamine, and adding p-toluenesulfonic acid based on the usage of catalyst after the reaction of 10-15 hours, wherein the mol ratio of the difluoro Gamma-ketone acid methyl ester to 1,2-ethylenediamine is (1-1.2) / 1, and the reflux reaction takes 10-15 hours, then the reaction is over, yellow liquid obtained through separation and purification is exactly the 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-alpha]imidazole-5(6H)-ketone, In the invention, the raw materials are easily available, the operation is simple, and synthesis by the one-pot is adopted the yield reaches 64%, thus being suitable for mass production.

Description

Technical field: [0001] The present invention relates to 7a-(difluoromethyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-5(6H)-one and its synthesis method. Background technique: [0002] So far, there are more than 20 million registered compounds, about half of which contain heterocyclic structures. Many important substances such as vitamins, hormones, antibiotics, alkaloids, etc., as well as some clinically effective synthetic drugs and pesticides such as corrosion inhibitors, anti-aging drugs, etc., all contain the structure of heterocyclic compounds. This has set off an upsurge of people's research on heterocyclic compounds. [0003] Pyrrolidone compounds are also a class of compounds with high application value. They are important pharmaceutical intermediates for the production of Naofukang, Maryland, etc., and are also raw materials for the production of polyvinylpyrrolidone. There are also some pyrrolidone compounds used in cosmetic moisturizers, such as sodium pyrrolidone ...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 郝健侯明华庄红伟万文蒋海珍
Owner SHANGHAI UNIV
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