ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate → (6R*,9aS*)-6-(4-fluorophenyl)-3-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-4-one

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate (220 mg) in methanol (5 mL) was cooled to −78° C., and ozone gas was bubbled through the reaction solution for 20 minutes. Sodium borohydride (164 mg) was added to the reaction solution while stirring at −78° C., and the reaction solution was stirred at that temperature for 30 minutes. Ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 26 mg of the title compound. The property values of the compound are as follows.

Provenance & Evidence