Sodium Hydroxide → HCID 66976421, compound

Participants

Reaction Steps

To a solution of aluminum(III) chloride (1.12 g) in diethyl ether (85 mL)-THF (40 mL) was added, under a nitrogen stream, lithium aluminum hydride (960 mg) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C., a solution of (6RS,7SR)-4-benzyl-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3-chloro-4-fluorophenyl)-1,4-oxazepan-3-one (6.72 g) in THF (60 mL) was added dropwise, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added 1 N aqueous sodium hydroxide solution (14 ml) at −78° C., the mixture was stirred at room temperature for 2 hr, and filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (4.16 g).

Provenance & Evidence