Methyl morpholine oxide → HCID 59333301, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-{[7-(trifluoromethyl)-8-vinylimidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol (110 mg; 0.32 mmol; 1 eq), osmium tetroxide (2.5% in tert-butanol, 166 mg; 0.016 mmol; 0.05 eq), N-methylmorpholine oxide (76 mg; 0.654 mmol; 2 eq) in acetone (3 ml) and water (0.33 ml) is stirred at 30° C. during 3 days. A suspension of sodium periodate (280 mg; 1.31 mmol; 4 eq) in water (1.6 ml) is then added and the resulting reaction mixture is stirred at 30° C. during 16 h. Partition (aqueous sodium sulfite/ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product as an off-white powder (64 mg; 0.19 mmol; 59%).

Provenance & Evidence