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Method for catalyzing dynamic kinetic resolution of arylamine via racemization catalyst

A racemization catalyst, a technology for catalyzing arylamines, applied in organic chemistry methods, organic chemistry, chemical recovery, etc.

Inactive Publication Date: 2012-07-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction temperature is generally too high (70~100 oC, most of them are 90 oC or 100 oC), and the reaction rate is relatively low. Slow, poor selectivity and stability, which greatly reduces the scope of application of chemical resolution

Method used

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  • Method for catalyzing dynamic kinetic resolution of arylamine via racemization catalyst
  • Method for catalyzing dynamic kinetic resolution of arylamine via racemization catalyst
  • Method for catalyzing dynamic kinetic resolution of arylamine via racemization catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Add p-chlorophenol, p-chlorophenyl valerate, dicyclohexylcarbodiimide and 4-dimethylaminopyridine with a molar ratio of 1:1:1:0.03, stir for 7 hours, filter, and dry the filtrate Bathing, concentrating, and passing through the column to obtain p-chlorophenyl propionate as an acyl donor for subsequent use;

[0024] 2) Under vigorous stirring, add 10 mL of an aqueous solution of magnesium chloride and aluminum chloride with a molar percentage of 3:1 to 200 mL of 3 mol / L sodium hydroxide solution, and stir for 10 minutes under nitrogen protection. Centrifuge, wash twice with deionized water, and disperse in 40 mL of deionized water. Placed in a 60 mL stainless steel reactor, at 100 o C hydrothermal treatment for 10 hours to prepare chloride ion intercalated hydrotalcite. Add it to 100 mL of 2 mol / L sodium lauryl sulfate aqueous solution, 80 o C for 12 hours at reflux. Cooling, centrifugation, filtration, washing with water, washing with acetone, 80 o Dried for 4 ho...

Embodiment 2

[0028] 1) Add p-chlorophenol, n-valeric acid, dicyclohexylcarbodiimide, and 4-dimethylaminopyridine in a molar ratio of 1: 2: 2: 0.05, stir for 7 hours, filter, dry the filtrate, concentrate, pass column, obtain p-chlorophenyl valerate as an acyl donor for subsequent use;

[0029] 2) Under vigorous stirring, add 15 mL of an aqueous solution of magnesium chloride and aluminum chloride with a molar percentage of 4:1 to 250 mL of 3 mol / L sodium hydroxide solution, and stir for 30 minutes under nitrogen protection. Centrifuge, wash with deionized water three times, and disperse in 40 mL of deionized water. Placed in a 60 mL stainless steel reactor, at 100 o C Hydrothermal treatment for 16 hours prepared chloride ion intercalated hydrotalcite. Add it to 100 mL of 2 mol / L sodium lauryl sulfate aqueous solution, 80 oC for 12 hours at reflux. Cooling, centrifugation, filtration, washing with water, washing with acetone, 80 o Dried for 4 hours at C to obtain dodecyl sulfate interc...

Embodiment 3

[0033] 1) Add p-chlorophenol, n-valeric acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a molar ratio of 1:2:2:0.05, stir for 3 hours, filter, dry the filtrate, concentrate, Go through the column to obtain p-chlorophenyl valerate as an acyl donor for subsequent use;

[0034] 2) Under vigorous stirring, add 10 mL of an aqueous solution of magnesium chloride and aluminum chloride with a molar percentage of 3:1 to 200 mL of 3 mol / L sodium hydroxide solution, and stir for 10 minutes under nitrogen protection. Centrifuge, wash twice with deionized water, and disperse in 40 mL of deionized water. Placed in a 60 mL stainless steel reactor, at 100 o C hydrothermal treatment for 10 hours to prepare chloride ion intercalated hydrotalcite. Add it to 100 mL of 2 mol / L sodium lauryl sulfate aqueous solution, 80 o C for 12 hours at reflux. Cooling, centrifugation, filtration, washing with water, washing with acetone, 80 o Dried for 4 hours at C to obtain dodecyl sulfate i...

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Abstract

The invention discloses a method for catalyzing dynamic kinetic resolution of arylamine via a racemization catalyst, comprising the following steps of: 1) adding p-chlorophenol, n-pentanoic acid, dicyclohexylcarbodiimide and 4-dimethylamino-pyridine, and carrying out mixing, filtration, drying, concentration and column chromatography to obtain a pentanoic acid p-chlorophenyl ester acyl donor; 2) carrying out coprecipitation on magnesium chloride solution and aluminum chloride solution and carrying out water-heat treatment to obtain chloridion intercalated hydrotalcite, adding the chloridion intercalated hydrotalcite in lauryl sodium sulfate aqueous solution, and carrying out backflow, cooling, centrifugation, water washing, acetone washing and drying to obtain a carrier; 3) adding palladium salt and the carrier, and carrying out heating, ascorbic acid addition, centrifugation, water washing, acetone washing and freeze-drying to obtain the racemization catalyst; and 4) adding arylamine, the acyl donor, lipase and the racemization catalyst in toluene and placing in a stainless steel reactor to add hydrogen so as to obtain amide. The method provided by the invention is used for catalyzing the dynamic kinetic resolution of arylamine, has rapid reaction rate, low temperature, high conversion rate and high product optical purity, and has great application value.

Description

field of invention [0001] The invention relates to a dynamic kinetic resolution method, in particular to a method in which a racemization catalyst is used to catalyze the dynamic kinetic resolution of arylamine. Background technique [0002] Various monochiral arylamines are very important chiral synthons, and are indispensable intermediates in the synthesis of medicines, agricultural chemicals, daily necessities, pheromones and high-quality liquid crystals, and are also important in asymmetric synthesis. important chiral auxiliaries. . Dynamic Kinetic Resolution (DKR) adds the in-situ racemization of the less reactive enantiomer on the basis of kinetic resolution, and the resolution process is followed by the in-situ racemization of the substrate in the same system Or at the same time, that is, one enantiomer is continuously converted into a product, and the other enantiomer is continuously racemized, so that the conversion rate of the substrate and the yield of the produ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/02C07B55/00
CPCY02P20/582
Inventor 符思敏徐刚吴坚平杨立荣
Owner ZHEJIANG UNIV
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