Sodium Bicarbonate → (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-hydroxypropoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Participants

Reaction Steps

A solution (1R,2S,3S,4R,55)-1-(acetoxymethyl)-5-(3-(4-(2-(tert-butyldimethylsilyloxy)propoxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (350 mg, 0.46 mmol) in Acetic acid:THF:Water (3:1:1, 5.0 mL) was stirred at r.t. for 48 h. After completion of the reaction, as confirmed by TLC, sat. solution of NaHCO3 (10 mL) was added dropwise to the reaction mixture and organic layer was extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4 and evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1:1 Ethyl acetate:Pet. Ether) to afford title compound (190 mg, 65.7%).

Provenance & Evidence