Ceric ammonium nitrate → 5-Cyclohexyl-2-(3-hydroxy-propyl)-morpholin-3-one

Participants

Reaction Steps

To a solution of 2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one (400 mg, 0.84 mmol, 1.0 equiv) in CH3CN (0.3 mL) and water (0.3 mL) was added CAN (922 mg, 1.68 mmol, 2.0 equiv). The mixture was stirred at room temperature for 1 hour then second portion of CAN (900 mg) was added. After stirred at room temperature for 1 hour, the reaction mixture was diluted with EtOAc and the phases were separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 50% to 100% EtOAc to give 5-cyclohexyl-2-(3-hydroxy-propyl)-morpholin-3-one 134 mg.

Provenance & Evidence