Calcium triflate catalyzed regioselective nucleophilic ring opening of epoxides to afford beta-aminoalcoholsCalcium triflate catalyzed regioselective nucleophilic ring opening of epoxides to afford beta-aminoalcohols
SyntheticPage 560
Published May 21, 2012
To a solution of epichlorohydrin (1.4 mL, 10 mmol) and 3-chloroaniline (2.3 mL,10 mmol) in acetonitrile (30 ml), calcium triflate (1.8 g, 5 mmol) was added and the reaction mixture was stirred at 60 oC overnight. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue. The product was extracted with dichloromethane (3 x 20 ml) and the combined organic layer was washed with brine (2 x 20 ml), dried over anhydrous Na2SO4 and evaporated under reduced pressure to obtain the crude product, which was purified by column chromatography over silica gel using ethyl acetate-petroleum ether (3:97 to 12:88) as eluent to afford pure 1-Chloro-3-(3'-chlorophenylamino)-propan-2-ol (92 % yield).