Water → HCID 10181711, compound

Participants

Reaction Steps

Aluminum chloride (913 mg, 6.9 mmol) was added to THF (10 mL) under ice cooling, and allowed to warm to room temperature so as to dissolve the aluminum chloride. The mixture was cooled with ice cooling and then lithium aluminium hydride (260 mg, 6.9 mmol) was added. After stirring for 15 minutes, A solution of (3R)-1-(2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-phenylpiperidine-2,6-dione obtained in Example 23 (640 mg, 1.4 mmol) in THF (5 ml) was added to the mixture under ice cooling. After the mixture was refluxed for 2 hours, the resulting mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=25/1) to obtain 350 mg (yield 58%) of the title compound via recrystallization (hexane). mp. 137–140° C.

Provenance & Evidence