Sodium periodate → 9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde

Participants

Reaction Steps

To a homogeneous solution of 1-(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)ethane-1,2-diol (Preparation 60E, 0.074 g, 0.139 mmol) in a mixture of THF (2.0 mL) and water (0.13 mL) at room temperature was added sodium periodate (0.045 g, 0.209 mmol). The reaction mixture was stirred for 60 min. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate, washed with water, and washed with brine. The organic layer was collected, and the combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford a quantitative yield of 9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde as a yellow oil. The product had an HPLC ret. time=3.02 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=499.9.

Provenance & Evidence