Potassium Carbonate → 593249-19-5

HRID 1418664Notes

Reaction equation

HRID 1418664 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 21916586593249-19-5Yield 113.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-pyrrolidinol (1.82 g) and 3,4-difluoronitrobenzene (3.0 g) in dimethylformamide (30 ml) was added potassium carbonate (3.94 g). The mixture was stirred at room temperature overnight and then filtered followed by washing with dichloromethane. The filtrate combined was concentrated under reduced pressure. The residue obtained was chromatographed over a silica gel column eluting with ethyl acetate/hexane with increasing in the content of ethyl acetate (50% to 60%). The appropriate fractions were pooled and concentrated under reduced pressure to give the title compound (4.83 g); 1H NMR (CD3OD, 270 MHz), δ 0.85 (2H, m), 2.25-2.57 (4H, m), 3.26 (1H, m), 5.47 (1H, t, J=8.6 Hz), 6.62 (1H, dd, J=2.4, 14.0 Hz), 6.69 (1H, dd, J=2.4, 8.6 Hz).

Workup

  1. filtrationfiltered
  2. washby washing with dichloromethane
  3. concentrationThe filtrate combined was concentrated under reduced pressure
  4. customThe residue obtained
  5. customwas chromatographed over a silica gel column
  6. washeluting with ethyl acetate/hexane
  7. temperaturewith increasing in the content of ethyl acetate (50% to 60%)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2847fd54f4824f13a990ba246f036cb5
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

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