Ethanol → HCID 131732774, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-((5-oxocyclopent-1-en-1-yl)oxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (150 mg, 0.22 mmol) in ethanol (1.14 mL), O-methoxylamine.hydrochloride (35 mg, 0.45 mmol) and pyridine (0.91 mL, 1.14 mmol) were added. The reaction mixture was heated to 100° C. for 1 h. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and the mixture was washed with 2% HCl (2×10 mL), water (50 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1.5:8.5 Acetone:hexane) to provide title compound (110 mg, 70.2%) as off-white solid.

Provenance & Evidence