Sodium Sulfite → HCID 86749318, compound

Participants

Reaction Steps

(1S, 2S, 3aR, 8bS)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl methyl ketone (112) (1.57 g) was dissolved in methylene chloride (30 ml) followed by the addition of sodium hydrogencarbonate (2.12 g) and metachloroperbenzoic acid (potency: 70%, 4.61) and stirring for 5 hours at room temperature. A 4% aqueous solution of sodium sulfite (100 ml) was added to the reaction mixture followed by extraction with methylene chloride (100 ml+50 ml×2). The organic layer was washed with saturated brine (50 ml×2) and concentrated to a solid after drying with anhydrous magnesium sulfate. The residue was purified with column chromatography (silica gel: n-hexane/ethyl acetate 1:1-1:2) to obtain (1S, 2S, 3aR, 8bS)-1-benzenesulfonamido-2-hydroxy- 2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl acetate (1.26 g).

Provenance & Evidence