Pyridine → HCID 117761600, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(4-acetylphenoxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (300.0 mg, 0.43 mmol) in ethanol (5 mL) under nitrogen atmosphere, was added pyridine (0.17 mL, 2.15 mmol) and O-ethylhydroxylamine hydrochloride (84.0 mg, 0.86 mmol). The reaction mixture was heated at 80° C. for 4 h. After completion of the reaction as confirmed by TLC, the crude compound was diluted with ethyl acetate (2×20 mL). The organic layer was separated, washed with 5% HCl (10 mL), water (10 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1:4 EtOAc:Pet Ether) to afford the title compound (230.0 mg, 72%) as a white solid.

Provenance & Evidence