Hydrogen Peroxide → HCID 178526290, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 2.0 mL, 39 mmol) was added dropwise to a stirred solution of TFAA (5.4 mL, 39 mmol) in DCM (50 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 84 (1.50 g, 4.6 mmol) and TFA (1.5 mL, 19.5 mmol) in DCM (50 mL) at 0° C. The solution was stirred at 20° C. for 6 h, diluted with dilute aqueous NH3 solution (30 mL) and extracted with DCM (3×150 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 85 (846 mg, 35%) as a red gum: 1H NMR δ 8.25 (s, 1H, H-9), 8.20 (s, 1H, H-5), 3.22-3.22 (m, 6H, 3×CH2), 3.11-3.20 (m, 4H, H-6, H-8), 2.80-3.05 (m, 2H, CH2), 2.33-2.43 (m, 2H, CH2), 2.21-2.30 (m, 2H, H-7), 2.13 (br s, 4H, 2×CH2); 13C NMR δ 155.4, 152.4, 151.0, 139.0, 133.9, 115.7, 113.7, 54.2, 53.5 (2), 33.3, 32.8, 27.1, 25.4, 23.8, 23.2 (2); HRMS (FAB+) calcd for C17H23N4O2 (MH+) m/z 315.1821, found 315.1820.

Provenance & Evidence