Dimethyl Sulfoxide → HCID 10399170, compound

Temperature

110 °C

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).

1. extractionThe resulting solution was extracted with EtOAc (2×50 ml)
2. washThe combined organics were washed with saturated NaHCO3 (50 ml), water (50 ml) and saturated aqueous NaCl (50 ml)
3. customThe organic layer was separated
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting residue was purified
8. washeluting with a gradient of 50-100% EtOAc/Hex)

ORD record

ord-579bc5a5c18f4e60902f9c0f4ee3fb6d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710049B2