Potassium Carbonate → HCID 58930644, compound

HRID 1805280Notes

Reaction equation

HRID 1805280 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.[NH2:15][C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.ClCCl>[NH2:15][C@H:16]1[CH2:20][CH2:19][N:18]([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)[CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1519351(3S)-(-)-3-AminopyrrolidineHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 58930644HCID 58930644, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of tert-butyl 4-fluorobenzoate (1, 1.00 g, 5.1 mmol), (S)-3-aminopyrrolidine (1.5 eq) and K2CO3 (0.84 g, 6.1 mmol, 1.2 eq.) is suspended in 4 mL of anhydrous DMSO. The suspension is stirred at 135° C. under N2 for 16 h in a sealed flask, cooled to room temperature, diluted with dichloromethane (300 mL) and successively washed with saturated aqueous NaHCO3 and water, dried over MgSO4, filtered and concentrated in vacuo to afford title compound 17 (1.22 g, 91% yield). 1H NMR: (DMSO-d6) δ(ppm): 7.65 (d, J=8.8 Hz, 2H), 6.47 (d, J=9.0 Hz, 2H), 3.65 (quint, J=5.3 Hz, 1H), 3.40 (t, J=9.8 Hz, 1H), 3.38 (t, J=9.8 Hz, 1H), 3.29-3.23 (m, 1H), 2.91 (dd, J=9.8, 4.7 Hz, 1H), 2.03 (sext, J=5.9 Hz, 1H), 1.74-1.63 (m, 3H), 1.48 (s, 9H). m/z: 263.1 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. washsuccessively washed with saturated aqueous NaHCO3 and water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1c6e7ba98e34969ab7473b8661b294e
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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