p-Fluoronitrobenzene → (S)-1-(4-nitro-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 469728

반응식

HRID 469728 반응식
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.[Cl-].[NH4+]>CS(C)=O>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10888648tert-Butyl 5-oxo-L-prolinate

생성물 1

HCID 67456456(S)-1-(4-nitro-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of (S)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (1.85 g, 10 mmol) in dimethylsulfoxide (10 mL) at room temperature, sodium hydride (440 mg of 60% dispersion in mineral oil, 11 mmol) is added in portions over a period of 20 min. After 30 min, 4-fluoronitrobenzene (1.06 mL, 10 mmol) is added and the mixture is heated by placing in an oil-bath maintained at 80° C. for 4 h. The reaction mixture is allowed to cool to room temperature, treated with saturated ammonium chloride solution (150 mL) and extracted with ethyl acetate (250 mL). Organic extracts are combined, washed with brine (100 mL), dried over anhydrous Na2SO4 and solvent removed in vacuo. The crude is purified chromatography over silica gel eluting with hexanes/ethyl acetate and the title compound is obtained as a light yellow solid, ESI m/z 307 [M+H]+.

후처리

  1. temperaturethe mixture is heated
  2. customby placing in an oil-bath
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate (250 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customremoved in vacuo
  8. customThe crude is purified chromatography over silica gel eluting with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-222aa04b76424d3fbacd196df57fa757
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629157B2

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