Potassium Carbonate → HCID 58417032, compound

HRID 1805285Notes

Reaction equation

HRID 1805285 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O>[OH:20][C@H:17]1[CH2:18][CH2:19][N:15]([C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 58417032HCID 58417032, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of tert-butyl 4-fluorobenzoate (1 g, 5.1 mmol) and (S)-pyrrolidin-3-ol (462 mg, 5.3 mmol) in DMSO (10 mL) was added powdered potassium carbonate (705 mg, 5.1 mmol). The mixture was stirred at 130° C. for 4 h and allowed to cool down to room temperature. The mixture was diluted with EtOAc (300 mL) and the solution was washed with water (2×100 mL), dried over Na2SO4, filtered and concentrated to provide title compound 157 (1.23 g, 88% yield) that was used in the next step without further purification. LRMS (ESI): (calc) 263.15 (found) 264.1 (MH+).

Workup

  1. temperatureto cool down to room temperature
  2. washthe solution was washed with water (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b16be6faf594cd6b53219e4886b8d20
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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