Hydrogen Peroxide → HCID 178495918, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 2.0 mL, 39 mmol) was added dropwise to a stirred solution of TFM (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 80 (1.50 g, 4.2 mmol) and TFA (1.5 mL, 1.95 mmol) in DCM (50 mL) at 0° C. The solution was stirred at 20° C. for 6 h, diluted with dilute aqueous NH3 solution (36 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 81 (533 mg, 35%) as a red gum: 1H NMR δ 8.28 (s, 1H, H-9), 8.24 (s, 1H, H-5), 3.78 (br t, J=4.7 Hz, 4H, 2×CH2O), 3.40-3.45 (m, 6H, 3×CH2), 3.33 [s, 6H, 2×OCH3), 3.19-3.23 (m, 2H, CH2), 3.12-3.17 (m, 4H, H-6, H-8), 2.34-2.38 (m, 2H, CH2), 2.22-2.28 (m, 2H, H-7); 13C NMR δ 155.5, 152.5, 151.1, 139.0, 134.0, 115.8, 113.8, 67.2 (2), 58.9 (2), 52.9 (3), 33.4, 32.9, 27.2, 25.5, 18.8; HRMS (FAB+) calcd for C19H29N4O4 (MH+) m/z 377.2189, found 377.2185.

Provenance & Evidence