Water → HCID 71008858, compound

Participants

Reaction Steps

To a cooled (−35˜−40° C.) solution of 5-Benzyl-2-(4-trifluoromethoxy-phenyl)-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione (0.6 g, 0.5 mmol) and CeCl3.7H2O (0.56 g, 0.5 mmol) in 250 mL EtOH/dichloromethane (1.5:1) were sequentially added NaBH4 (0.057 g, 10 mmol). The temperature was kept at −35˜−40° C. for 2 h, poured into cold water (100 mL) and extracted with dichloromethane (2×80 mL). After washing the organic phase with brine (100 mL) and drying over anhydrous Na2SO4, the solvent was removed and the crude product was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (5:1 to 2:1) to yield the title compound (0.17 g, 29%). 1H NMR (300 MHz, CDCl3): δ 7.78 (d, 2H, J=9.0 Hz), 7.38-7.22 (m, 7H), 5.52 (d, 1H, J=6.9 Hz), 3.69 (q, 2H, J=12.6 Hz), 3.20-3.18 (m, 3H), 3.07 (bs, 1H), 2.52 (t, 1H, J=10.1 Hz), 2.31-2.28 (m, 1H); LC-MS: [M+1]+ 393.0.

Provenance & Evidence