1.1: sodium tetrahydroborate; pyridine / methanol / 9 h / |Reflux 2.1: bromine; sodium acetate; acetic acid 3.1: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 4.1: borane-THF / ethanol; tetrahydrofuran / 13 h 5.1: triethylamine / dichloromethane / 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / |Reflux 7.1: ethanol 8.1: sodium hydroxide / ethyl acetate 8.2: 18 h / |Reflux View Scheme

pyridine; methanol; sodium tetrahydroborate T=100°C; 9 h;

1: With diisobutylaluminium hydride in toluene T=-78°C; 2: With hydrogenchloride in toluene T=20°C; 0.0333333 h;