反应详情

To a solution of 3-Hydroxy-5-methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one (0.1 g, 0.32 mmol) in trifluoroacetic acid (20 mL) was added NaCNBH3 (0.04 g, 0.64 mmol) at −20° C., and the mixture was stirred for 1 h. Water (30 mL) was added. The mixture was extracted with dichloromethane (3×20 mL), washed with brine (50 mL), and dried over anhydrous Na2SO4. The solvent was removed by reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (10:1 to 5:1) to yield the title compound (40 mg, 40%). 1H NMR (300 MHz, CDCl3): δ 7.69-7.64 (m, 2H), 7.25-7.19 (m, 2H), 4.91 (s, 2H), 4.07-4.01 (m, 1H), 3.54-3.49 (m, 1H), 3.19-3.12 (m, 1H), 2.96-2.71 (m, 4H), 2.25-2.18 (m, 1H); LC-MS: [M+1]+ 298.1.

1. extractionThe mixture was extracted with dichloromethane (3×20 mL)
2. washwashed with brine (50 mL)
3. dry with materialdried over anhydrous Na2SO4
4. customThe solvent was removed by reduced pressure
5. customThe residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (10:1 to 5:1)