trimethylsilyl trifluoromethanesulfonate in dichloromethane T=0°C; 2.5 h;

1: n-Bu3SnCl 2: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol 3: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature 4: 74 percent / pyridine / Ambient temperature 5: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C View Scheme

1: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature 2: 74 percent / pyridine / Ambient temperature 3: 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 View Scheme

1: LiNH2 / liquid ammonia 2: PBr3, 2.6-lutidine / diethyl ether 3: n-Bu3SnCl 4: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol 5: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature 6: 74 percent / pyridine / Ambient temperature 7: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C View Scheme

1: PBr3, 2.6-lutidine / diethyl ether 2: n-Bu3SnCl 3: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol 4: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature 5: 74 percent / pyridine / Ambient temperature 6: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C View Scheme

1: 74 percent / pyridine / Ambient temperature 2: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C View Scheme

sodium tetrahydroborate; diisobutylaluminium hydride Yield given. Multistep reaction;