Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

(4ar,8ar)-3a-(difluoromethyl)decahydro-1h-benzene[d]pyrrole[1,2-a]-thiazole-1-ketone and synthesis method thereof

A technology of difluoromethyl and synthetic methods, applied in (4aR), can solve the problems that have not been reported, and achieve the effects of high fat solubility and hydrophobicity, easy availability of raw materials, and strong physiological activity

Inactive Publication Date: 2009-09-30
SHANGHAI UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • (4ar,8ar)-3a-(difluoromethyl)decahydro-1h-benzene[d]pyrrole[1,2-a]-thiazole-1-ketone and synthesis method thereof
  • (4ar,8ar)-3a-(difluoromethyl)decahydro-1h-benzene[d]pyrrole[1,2-a]-thiazole-1-ketone and synthesis method thereof
  • (4ar,8ar)-3a-(difluoromethyl)decahydro-1h-benzene[d]pyrrole[1,2-a]-thiazole-1-ketone and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of (4aR, 8aR)-3a-(difluoromethyl)decahydro-1H-benzo[d]pyrrole[1,2-a]-imidazol-1-one adopts the following steps: ① at 50 Add 0.40 g of ethyl difluoro-γ-ketoate, 0.019 g of p-toluenesulfonic acid, 25 ml of toluene, and 0.2 g of anhydrous magnesium sulfate into a 1 ml round-bottomed flask equipped with a reflux condenser. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 0.228 g of (1R,2R)-1,2-cyclohexanediamine was added; ② The reaction solution 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 6:1 to...

Embodiment 2

[0032] Example 2: Preparation of (4aR, 8aR)-3a-(difluoromethyl)decahydro-1H-benzo[d]pyrrole[1,2-a]-imidazol-1-one adopts the following steps: ①at 250 Add 10 grams of ethyl difluoro-γ-ketoate, 0.475 grams of p-toluenesulfonic acid, 150 milliliters of toluene, and 5 grams of anhydrous magnesium sulfate into a round-bottomed flask equipped with a reflux condenser. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 5.7 g of (1R,2R)-1,2-cyclohexanediamine was added; ② The reaction solution 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 concentrate was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume rati...

Embodiment 3

[0033] Example 3: Preparation of (4aR, 8aR)-3a-(difluoromethyl)decahydro-1H-benzo[d]pyrrole[1,2-a]-imidazol-1-one adopts the following steps: ①In 2 Add 100 grams of ethyl difluoroγ-ketoate, 4.75 grams of p-toluenesulfonic acid, 1000 milliliters of toluene, and 20 grams of anhydrous magnesium sulfate into a 1-liter round-bottomed flask equipped with a reflux condenser. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 57 g of (1R,2R)-1,2-cyclohexanediamine was added. ② The reaction product gradually turned yellow under reflux. After 12 hours of reaction, 4.75 g of p-toluenesulfonic acid was added. The reaction was continued for 20 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to (4aR,8aR)-3a-(difluoromethyl)decahydro-1H-benzene[d]pyrrole[1,2-a]-thiazole-1-ketone and a synthesis method thereof. The structural formula of the compound is shown as right. The method comprises the following steps: dissolving difluoro gamma-methyl keto ester and catalytic dosage of paratoluenesulfonic acid into toluene, adding catalytic dosage of anhydrous magnesium sulfate, stirring the mixture to reflux for 20 to 60 minutes, and then adding (1R,2R)-1,2- cyclohexanediamine; adding the catalytic dosage of paratoluenesulfonic acid after continuously reacting for 10 to 15 hours, wherein the mol ratio of the difluoro gamma-methyl keto ester to the (1R,2R)-1,2-cyclohexanediamine is (1-1.2):1; performing reflux reaction for 10 to 15 hours, and ending the reaction; and performing separation and purification to obtain a yellow sticky liquid, namely the (4aR,8aR)-3a-(difluoromethyl)decahydro-1H-benzene[d]pyrrole[1,2-a]-thiazole-1-ketone. In the invention, raw materials are easy to obtain, the operation is simple, the product is synthesized by a one-pot method, the productivity is high up to 82 percent, and the product is suitable to be produced on a large scale.

Description

Technical field: [0001] The invention relates to a synthesis method of (4aR, 8aR)-3a-(difluoromethyl)decahydro-1H-benzo[d]pyrrole[1,2-a]-imidazol-1-one. Background technique: [0002] Since the advent of freon in the early 1930s, organic fluorine chemistry has been showing a vigorous development trend. Due to the introduction of fluorine atoms, organic and inorganic compounds show unique physical and chemical properties and physiological activities. Fluorine-containing compounds have a wide range of physiological activities and broad application prospects. The synthesis methods and medicinal properties of these compounds have received great attention. Its synthesis method has always been one of the research directions of organic fluorine chemistry. [0003] Heterocyclic compounds are widely distributed in nature, accounting for almost one-third of the known organic compounds, and have many uses. Many important substances such as chlorophyll and some natural medicines and ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 郝健侯明华庄红伟万文蒋海珍
Owner SHANGHAI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com