Sodium cyanoborohydride → HCID 71009029, compound

Participants

Reaction Steps

To a solution of 5-Benzyl-3-hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrol-1-one (6.0 g, 15.3 mmol) in trifluoroacetic acid (50 mL) was added NaCNBH3 (1.0 g, 15.3 mmol) and the mixture was stirred at room temperature overnight. Trifluoroacetic acid was removed by reduced pressure and the residue was added to dichloromethane (50 mL). Saturate solution of Na2CO3 (70 mL) was added. The mixture was extracted with dichloromethane (2×60 mL), washed with brine (100 mL), dried over Na2SO4. The solvent was removed and the crude product was purified by column chromatography on silica gel with petroleum ether:ethyl acetate (10:1 to 5:1) to yield the title compound (4.0 g, 70%). 1H NMR (300 MHz, CDCl3): δ 7.73-7.69 (m, 2H), 7.31-7.22 (m, 7H), 4.04 (t, 1H, J=9.5 Hz), 3.74-3.54 (m, 3H), 3.28-3.17 (m, 2H), 2.95 (bs, 1H), 2.76-2.74 (m, 1H), 2.63-2.53 (m, 2H); LC-MS: [M+1]+ 376.9.

Provenance & Evidence