1: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol 2: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature 3: 74 percent / pyridine / Ambient temperature 4: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C View Scheme

1: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol 2: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature 3: 74 percent / pyridine / Ambient temperature 4: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C 5: 1) diisobutylaluminium hydride, 2) sodium borohydride View Scheme