Water → HCID 69073065, compound

Participants

Reaction Conditions

Reaction Steps

Triethylsilane (5.5 mL) and trimethylsilyl trifluoromethanesulfonate (442 μL) were added to a solution of (R*)-4-(4-fluorophenyl)-1-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-6-one (324 mg) in dichloromethane (10 mL), and the reaction solution was reacted at room temperature for 1.5 hours. Then, the reaction solution was heated to 60° C. and stirred for two hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 69.2 mg of (R*)-4-(4-fluorophenyl)-3,4,8,9-tetrahydro-7H-pyrido[2,1-c][1,4]oxazin-6-one and 52.8 mg of (4R*,9aR*)-4-(4-fluorophenyl)hexahydropyrido[2,1-c][1,4]oxazin-6-one. The physical properties of (R*)-4-(4-fluorophenyl)-3,4,8,9-tetrahydro-7H-pyrido[2,1-c][1,4]oxazin-6-one are as follows.

Provenance & Evidence