Pyridine → (6R,9aR)-1,1-dimethyl-6-(3,4,5-trifluorophenyl)tetrahydro [1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

Participants

Reaction Steps

Under ice-cooling, oxalyl chloride (205 μL) was added dropwise into a chloroform (10 mL) solution of pyridine (2 mL) and 2-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]propane-2-ol (330 mg). The reaction solution was stirred for 1 hour at the same temperature, and the resultant was stirred a further 2 hours at room temperature. Water was added to the reaction solution, and the organic layer was partitioned. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. The residue was purified by silica gel column chromatography (heptane/ethyl acetate), and the title compound (260 mg) was obtained. The physical property values are as follows.

Provenance & Evidence