Ozone → 2-(4-Trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione

Participants

Reaction Steps

A slow stream of ozone was bubbled into a solution of 5-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one (0.1 g, 0.34 mmol) in 30 mL of methylene chloride at −78° C. The stream of ozone was maintained until a slight blue color persisted. After removal of excess ozone with a stream of nitrogen, 2 mL of dimethyl sulfide was added at −78° C. The mixture was then allowed to warm to room temperature, and stirred for overnight. The solvent was removed, and the crude product was purified by prep-TLC (MeOH: dichloromethane=1:50) to yield the title compound (50 mg, 50%). 1H NMR (300 MHz, CDCl3): δ 7.69-7.65 (m, 2H), 7.26-7.22 (m, 2H), 4.20 (t, 1H, J=8.4 Hz), 3.69-3.66 (m, 1H), 3.45-3.38 (m, 1H), 3.22-3.16 (m, 1H), 2.88-2.56 (m, 3H), 2.25-2.18 (m, 1H); LC-MS: 300.1 [M+1]+.

Provenance & Evidence