Sodium Sulfite → HCID 86749315, compound

Participants

Reaction Steps

(1R, 2R, 3aS, 8bR)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta [b]benzofuran-5-yl methyl ketone (111) (219 mg) was dissolved in methylene chloride (4 ml) followed by the addition of sodium hydrogencarbonate (197 mg, 2.3 mmol) and metachloroperbenzoic acid (potency: 70%, 289 mg) and stirring for 2 hours at room temperature. A 3% aqueous solution of sodium sulfite (15 ml) was added to the reaction mixture followed by extraction with methylene chloride (15 ml+10 ml×2). The organic layer was washed with water (15 ml) and saturated brine (15 ml) and concentrated after drying with anhydrous magnesium sulfate. The residue was purified with column chromatography (silica gel: cyclohexane/ethyl acetate 1:2) to obtain (1R, 2R, 3aS, 8bR)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl acetate (190 mg).

Provenance & Evidence