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

HRID 1441364Notes

Reaction equation

HRID 1441364 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 86594863tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eda7af133160438ba551684c975ce4c0
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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