Hydrogen Peroxide → HCID 86646671, compound

Participants

Reaction Steps

One an one-half (1.5 g, 3.56 mmol) of (4R)-tert-butyl-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2yl))phenyl]-2-oxopyrrolidinecarboxylate was dissolved in 10 mL dichloromethane. To this solution, 3 equiv. of 35% hydrogen peroxide (10.68 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature. The mixture was diluted with saturated ammonium chloride aqueous solution and extracted with dichloromethane (3 times). The combined organic layers were dried over Na2SO4 and concentrated to dryness to provide tert-butyl (4R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidinecarboxylate (68a) as a clear oil (1.2 g, 95% yield). 1H-NMR (400 MHz, CD3OD): δ 2.63-2.69 (dd, J=17.2, 9.2 Hz, 1H), 2.80-2.87 (dd, J=17.2, 8.4 Hz, 1H), 3.47-3.54 (m, 1H), 3.61-3.66 (m, 1H), 4.12-4.11 (t, J=2.4 Hz, 1H), 7.24-7.22 (d, J=8.0 Hz, 1H), 6.82-6.82 (d, J=2.0 Hz, 1H), 6.73-6.75 (d, J=2.0 Hz, 1H); MS (ESI) m/z 334.01 (M+Na)+.

Provenance & Evidence