Sodium hydride → (2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-(3-fluoro-5-nitrophenoxy)pyrrolidine-1-carboxylate

HRID 495058

Reaktionsgleichung

Reaktionsgleichung von HRID 495058
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([OH:15])[CH2:13][CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[C:30](F)[CH:31]=1>CN(C=O)C>[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([O:15][C:30]2[CH:29]=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=[C:26]([F:25])[CH:31]=2)[CH2:13][CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 752721,3-Difluoro-5-nitrobenzeneHCID 14462925HCID 14462925, Verbindung

Produkt 1

HCID 57683630(2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-(3-fluoro-5-nitrophenoxy)pyrrolidine-1-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of (2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypyrrolidine-1-carboxylate (1equiv) in DMF (0.5 M) was added NaH (1.3 equiv) as a solid. After stirring for 15 min at 0° C., 3,5-difluoronitrobenzene (1.2 equiv) was added by syringe. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched by the addition of water, and the mixture was diluted with EtOAc. The organic layer was washed four times with water and once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography (0-20% EtOAc/Hexanes) provided the title compound in 82% yield.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 h
  3. customThe reaction was quenched by the addition of water
  4. additionthe mixture was diluted with EtOAc
  5. washThe organic layer was washed four times with water
  6. dry with materialonce with brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (0-20% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-22c5e1e745164e00bdcf270bb65eea2e
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538223B2

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