BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-

521284-21-9

391901-45-4

(R)-2-((4-nitrophenylethyl)amino)-1-phenylethanol hydrochloride (Compound I, 15 g, 0.0465 mol) was dissolved in 150 mL of methanol with stirring. Ammonium formate (14.6 g, 0.2325 mol) and 1.5 g of 10% palladium carbon catalyst were subsequently added. The reaction mixture was heated to 65 °C and kept at reflux for 5 hours. The reaction was monitored by thin layer chromatography (TLC, GF254 plate, unfolding agent ratio ethyl acetate:methanol = 5:1) until the fluorescent spots of compound I disappeared. Upon completion of the reaction, methanol was removed by concentration under reduced pressure, followed by the addition of water and ethyl acetate for extraction. The organic phase was evaporated under reduced pressure to remove ethyl acetate to give an off-white solid product (Compound II, 10.91 g) in 91.71% yield.