1.1: hydrogenchloride / water; acetic acid / 20 °C 2.1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 3.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 4.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 4.2: 20 °C 5.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 6.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 6.2: 120 °C View Scheme

hydrogenchloride in water; acetic acid T=20°C;

1: hydrogenchloride / water; acetic acid / 20 °C 2: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 3: borane-THF / tetrahydrofuran / 0 °C / Reflux View Scheme

1: hydrogenchloride / water; acetic acid / 20 °C 2: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr View Scheme

Multi-step reaction with 5 steps 1.1: hydrogenchloride / water; acetic acid / 20 °C2.1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr3.1: borane-THF / tetrahydrofuran / 0 °C / Reflux4.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C4.2: 20 °C5.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C