Acetic Acid → HCID 23121851, compound

Participants

Reaction Steps

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.51 mmol), acetic acid (0.045 mL, 0.79 mmol) and 1-benzyl-4-piperidone (0.12 g, 0.63 mmol) in tetrahydrofuran (5 mL) was added sodium triacetoxyborohydride (0.16 g, 0.75 mmol), and the mixture was stirred at room temperature for 16 hours. 1-Benzyl-4-piperidone (0.060 mL) and sodium triacetoxyborohydride (0.16 g) were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine, and then dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=98:2 to hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate-hexane to obtain the title compound (70 mg, yield 29%).

Provenance & Evidence