Potassium Carbonate → HCID 67427269, compound

HRID 1523400Notes

Reaction equation

HRID 1523400 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)(=O)=O)=CC=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Product 1

HCID 67427269HCID 67427269, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-4-nitro phenol (5 g, 0.032 moles), potassium carbonate (6.34 g, 0.047 moles) and tert-Butyl 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (14 g, 0.04 moles) in dimethylformamide (50 mL) were stirred at 100° C. After completion of reaction, the mass was quenched on to water (100 mL) and extracted with ethyl acetate (2×100 mL). The resulting organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to obtain the crude residue, which was further purified by flash chromatography using (ethyl acetate:hexane, 0.5:9.5) to afford the title compound 9.23 g (Yield: 85%).

Workup

  1. customAfter completion of reaction
  2. customthe mass was quenched on to water (100 mL)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe resulting organic layer was washed with brine solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain the crude residue, which
  8. customwas further purified by flash chromatography

Sources & evidence

ORD record
ord-8012e9c8e46b4483abc3060a834716c8
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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