Potassium Permanganate → HCID 68556586, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 6-bromo-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (2.1 g) obtained in Example 1, 8) in acetone (50 ml) was added potassium permanganate (7.9 g), and the mixture was cooled to 0° C. Iron trichloride (5.0 g) was added, and the mixture was stirred at 50° C. for 16 hr. The reaction solution was diluted with isopropanol (20 ml) and CHCl3 (20 ml), filtered through celite, and extracted with CHCl3. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=3:1) to give the title compound (681 mg, 31%, Rf=0.29 [hexane:ethyl acetate=3:1]) and tert-butyl 6-bromo-2,2,4,4-tetramethyl-2,3,7,8-hexahydro-1H-cyclopenta[h]quinoline-3,9-dione-1-carboxylate (293 mg, 13%, Rf=0.33 [hexane:ethyl acetate=3:1]).

Provenance & Evidence