Реакция #747281

Уравнение реакции

DMSO

3-(toluene-4-sulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester

Sodium hydride

dimethyl sulfoxide

(3,4-dichlorophenyl)-(4-fluorophenyl)amine

→

3-[(3,4-dichlorophenyl)-(4-fluorophenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester

Выход 17.5%

Растворители

Ethyl acetate

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at 60° C. for one hour
2. 2
   workup.ADDITIONwas gradually added to the mixture
3. 3
   workup.STIRRINGstirred at 60° C. for 15 hours
4. 4
   ПромывкаThe solution was then washed with water
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   Другоеthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)
8. 8
   workup.DISTILLATIONThe eluent solvent was distilled off under reduced pressure

Методика

Sodium hydride (0.19 g, 60% in oil) was added to 10 ml of dimethyl sulfoxide (DMSO) and stirred at 60° C. for one hour. Subsequently, 1.0 g of (3,4-dichlorophenyl)-(4-fluorophenyl)amine was added to the mixture and stirred at 60° C. for one hour. A DMSO solution containing 2.0 g of 3-(toluene-4-sulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester was gradually added to the mixture and stirred at 60° C. for 15 hours. Ethyl acetate was added to the reaction solution. The solution was then washed with water, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1). The eluent solvent was distilled off under reduced pressure to thereby obtain 0.29 g of oily brown 3-[(3,4-dichlorophenyl)-(4-fluorophenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester.

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