1: With borane-THF in tetrahydrofuran T=20°C; 12 h; 2: With ethanol in tetrahydrofuran 1 h; 3: With hydrogenchloride in tetrahydrofuran; diethyl ether

1: sodium tetrahydroborate; pyridine / methanol / 9 h / |Reflux 2: bromine; sodium acetate; acetic acid 3: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 4: borane-THF / ethanol; tetrahydrofuran / 13 h View Scheme

1: bromine; sodium acetate; acetic acid 2: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 3: borane-THF / ethanol; tetrahydrofuran / 13 h View Scheme

1: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 2: borane-THF / ethanol; tetrahydrofuran / 13 h View Scheme

1: sodium acetate; tetrabutylammomium bromide; tris-(o-tolyl)phosphine; 5 palladium on charcoal / N,N-dimethyl acetamide / 12 h / |Reflux 2: sodium tetrahydroborate; pyridine / methanol / 9 h / |Reflux 3: bromine; sodium acetate; acetic acid 4: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 5: borane-THF / ethanol; tetrahydrofuran / 13 h View Scheme

1.1: triethylamine / dichloromethane / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / |Reflux 3.1: ethanol 4.1: sodium hydroxide / ethyl acetate 4.2: 18 h / |Reflux 5.1: hydrogen; 10 palladium hydroxide on charcoal / acetic acid / 24 h / 20 °C / 3675.37 Torr View Scheme

1.1: triethylamine / dichloromethane / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / |Reflux 3.1: ethanol 4.1: sodium hydroxide / ethyl acetate 4.2: 18 h / |Reflux View Scheme