1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere 5: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 6: palladium 10 on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 7: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

diisobutylaluminium hydride in toluene T=-70°C;