Hydrogen Peroxide → HCID 178483401, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.65 mL, 13 mmol) was added dropwise to a stirred solution of TFAA (1.8 mL, 13 mmol) in DCM (20 mL) at 0° C. The solution was stirred at 0° C. for 5 min, warmed to 20° C. for 10 min, then cooled to 0° C. and added to a stirred solution of 1-oxide 78 (353 mg, 1.3 mmol) and TFA (0.7 mL, 9.1 mmol) in DCM (20 mL) at 0° C. The solution was stirred at 20° C. for 8 h, diluted with dilute aqueous NH3 solution (12 mL) and extracted with DCM (4×50 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1,4-dioxide 79 (154 mg, 41%) as a red solid: 1H NMR δ 8.30 (s, 1H, H-9), 8.26 (s, 1H, H-5), 3.25-3.09 (m, 6H, H-6, H-8, CH2), 2.75 (t, J=7.3 Hz, 2H, CH2), 2.70 [s, 6H, N(CH3)2], 2.29-2.14 (m, 4H, H-7, CH2); 13C NMR δ 155.2, 153.9, 150.8, 139.1, 133.9, 115.9, 113.9, 58.0, 44.3 (2), 33.4, 32.9, 27.9, 25.6, 21.7; HRMS (FAB+) calcd for C15H21N4O2 (MH+) m/z 289.1665, found 289.1669.

Provenance & Evidence