Dimethyl Sulfoxide → tert-Butyl (2S)-4-oxo-2-phenylpyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a flame dried flask equipped with stir bar was added 150 mL anhydrous dichloromethane which was cooled to −78° C. Oxalyl chloride (3.8 mL, 44 mmol) and DMSO (4.8 mL, 61 mmol) were added sequentially and the reaction stirred for 10 minutes. tert-butyl (2S,4S)-4-hydroxy-2-phenylpyrrolidine-1-carboxylate (2-2, 2.28 g, 8.73 mmol) in 10 mL anhydrous dichloromethane was added dropwise and stirred 1 hour at −78° C. Triethylamine (12 mL, 87 mmol) was added and the reaction was warmed to 0° C. over 1 hour. Upon completion, the reaction was washed with 5% NaHCO3, brine and dried over MgSO4. The organic layer was concentrated to provide crude tert-butyl (2S)-4-oxo-2-phenylpyrrolidine-1-carboxylate (2-3). Recrystallization was effected with EtOAc/hexanes. 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 3H), 7.17 (m, 2H), 5.38 (m, 1H), 4.08 (d, J=19.5 Hz, 1H), 3.90 (d, J=19.3 Hz, 1H), 3.13 (dd, J=18.8, 9.8 Hz, 1H), 2.58 (dd, J=18.6, 2.4 Hz, 1H), 1.40 (br s, 9H); MS 206.0 found, 206.1 (M−C(CH3)3) required.

Provenance & Evidence