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

HRID 2408856ノート

反応式

HRID 2408856 の反応式
[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]

参加物

6

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 24758Sodium hydrideHCID 13591085tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylateHCID 66657269(3,4-Dichlorophenyl)-(4-fluorophenyl)amine

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-608c411334fc45efa3219aab217d27fe
出典データセット
uspto-grants-2014_08
特許番号
US08815871B2

反応ノート

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