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

HRID 469728

Reaktionsgleichung

Reaktionsgleichung von HRID 469728
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-222aa04b76424d3fbacd196df57fa757
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629157B2

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