p-Fluoronitrobenzene → tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

HRID 1441364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441364
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:9]([O:8][C:7](=[O:13])[NH:6][C@@H:3]1[CH2:4][CH2:5][N:1]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:2]1)([CH3:10])([CH3:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Produkt 1

HCID 86594863tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamateAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

tert-Butyl(3R)-pyrrolidin-3-ylcarbamate (4.54 g, 24.4 mmol), 4-fluoronitrobenzene (3.78 g, 24 mmol) and potassium carbonate (3.54 g 25.6 mmol) in acetonitrile (70 ml) were heated under reflux for 18 hours. After evaporation under reduced pressure, the mixture was dissolved in DCM (200 ml), and washed with water (100 ml) and saturated sodium chloride solution (25 ml). The solution was dried and filtered. After evaporation under reduced pressure, chromatography on silica gel eluting with DCM gave the title compound (7.19 g, 97%). NMR: 1.39 (s, 9H), 1.87-1.98 (m, 1H), 2.09-2.21 (m, 1H), 3.15-3.23 (m, 1H), 3.32-3.44 (m, 1H), 3.45-3.51 (m, 1H), 3.53-3.61 (m, 1H), 4.09-4.21 (m, 1H), 6.57 (d, 2H), 7.21 (s, 1H), 8.01 (d, 2H); m/z (MH+—C4H8) 252.

Aufarbeitung

  1. temperatureunder reflux for 18 hours
  2. customAfter evaporation under reduced pressure
  3. dissolutionthe mixture was dissolved in DCM (200 ml)
  4. washwashed with water (100 ml) and saturated sodium chloride solution (25 ml)
  5. customThe solution was dried
  6. filtrationfiltered
  7. customAfter evaporation under reduced pressure, chromatography on silica gel eluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-eda7af133160438ba551684c975ce4c0
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655652B2

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