Potassium Carbonate → HCID 59737483, compound

HRID 1907754Notes

Reaction equation

HRID 1907754 reaction equation
C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8]1.F[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>CS(C)=O.CCOC(C)=O.O>[NH2:12][C@H:9]1[CH2:10][CH2:11][N:7]([C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)[CH2:8]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoateHCID 1519351(3S)-(-)-3-Aminopyrrolidine

Product 1

HCID 59737483HCID 59737483, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

K2CO3 (7.71 g, 55.84 mmol) was added to a solution of (S)-pyrrolidin-3-amine (5.0 g, 58.04 mmol) and methyl 4-fluorobenzoate (8.6 g, 55.81 mmol) in DMSO (20 mL). The reaction mixture was stirred for 18 h at 130° C. in a sealed tube. The reaction mixture was cooled, diluted with AcOEt and H2O, and extracted with AcOEt (3 times). The extract was washed with water, NH4Cl and brine, dried over MgSO4, filtered and concentrated to give the title compound 323 (7.98 g, 65% yield) as a pink solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with AcOEt (3 times)
  3. washThe extract was washed with water, NH4Cl and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-922c15e5ba894bb29b882853f6e65d1f
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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