Triethylamine → (3S)-2-oxo-1-[4-(trifluoromethyl)phenyl]pyrrolidin-3-yl 4-(trifluoromethyl)benzenesulfonate

Participants

Reaction Steps

To a dichloromethane (10 mL) solution of (3S)-3-hydroxy-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one (691 mg, 2.82 mmol), triethylamine (589 μL, 4.23 mmol), and 4-(dimethylamino)pyridine (69 mg, 0.56 mmol) at 0° C. was added a dichloromethane (10 mL) solution of 4-(trifluoromethyl)benzenesulfonyl chloride (827 mg, 3.38 mmol) dropwise. After stirring for 3 hours, the mixture was partitioned between diethyl ether (100 mL) and water (100 mL). The organic layer was washed with brine (2×100 mL), dried (magnesium sulfate) and concentrated to give the title compound, which was subjected to the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=7.9 Hz, 2H), 7.85 (d, J=7.4 Hz, 2H), 7.71 (d, J=8.6 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H), 5.25 (t, J=8.0 Hz, 1H), 3.98-3.93 (m, 1H), 3.85-3.81 (m, 1H), 2.81-2.75 (m, 1H), 2.49-2.43 (m, 1H).

Provenance & Evidence