Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 131724713, compound

Participants

Reaction Steps

5-tert-Butoxycarbonyloxy-7,7-diethyl-1a,2,7,7a-tetrahydro-1-aza-cyclopropa[b]naphthalene-1-carboxylic acid tert-butyl ester (224.0 mg, 0.54 mmol) placed under Argon at room temperature was dissolved in anhydrous ethanol (8.0 mL). To this solution was added a catalytic amount of pyridinium p-toluene sulfonate. The reaction mixture was stirred overnight. The next day, the reaction mixture was poured into an aqueous solution of sodium bicarbonate and it was extracted using dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and the solvent was removed. The crude was purified by flash chromatography using; hexanes:ethyl acetate (9:1) then (8:2) as the eluent. The isolated product is a solid (129 mg, 55%).

Provenance & Evidence