Dimethyl Sulfoxide → 3-[(3,4-Dichlorophenyl)-(4-fluorophenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1966018노트

반응식

HRID 1966018 반응식
[H-].[Na+].CS(C)=O.[Cl:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[Cl:14].[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(OCC)(=O)C>[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32]([N:15]([C:10]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=2)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

참가 물질

6

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 24758Sodium hydrideHCID 13591085tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylateHCID 66657269(3,4-Dichlorophenyl)-(4-fluorophenyl)amine

생성물 1

HCID 666572353-[(3,4-Dichlorophenyl)-(4-fluorophenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester수율 17.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d4efd9e4f57a49169370faef18479309
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420623B2

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