Dimethyl Sulfoxide → HCID 10399170, compound

Participants

Reaction Conditions

Reaction Steps

To a seal tube was added pyrrolidin-3-ol (1 gm, 11.48 mmol), ethyl 4-fluorobenzoate (2.90 gm, 17.22 mmol) and DMSO (20 ml). The reaction was stirred at 110° C. for 20 hrs. After this time, the reaction was diluted with water (50 ml). The resulting solution was extracted with EtOAc (2×50 ml). The combined organics were washed with saturated NaHCO3 (50 ml), water (50 ml) and saturated aqueous NaCl (50 ml). The organic layer was separated, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 50-100% EtOAc/Hex) to give the product ethyl 4-(3-hydroxypyrrolidin-1-yl)benzoate (1.52 g, 6.46 mmol, 56.3% yield) as white solid. Anal. Calcd. for C13H12NO3 m/z 235.3, found: 236.4 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.97-7.87 (m, 2H), 6.61-6.44 (m, 2H), 4.77-4.57 (m, 1H), 4.32 (q, J=7.1 Hz, 2H), 3.63-3.51 (m, 2H), 3.49-3.40 (m, 1H), 3.34 (d, J=10.8 Hz, 1H), 2.27-2.03 (m, 2H), 1.73 (d, J=4.4 Hz, 1H), 1.37 (t, J=7.1 Hz, 3H).

Provenance & Evidence