hydrogen; palladium on activated charcoal in ethanol

1: hydrogen / Pd/C / ethanol 2: NaOH / H2O; ethanol / 25 °C View Scheme

lithium aluminium tetrahydride

1: triethylamine, 4-(dimethylamino)pyridine / tetrahydrofuran / 16 h / Ambient temperature 2: 1.0 N LiOH / dioxane / 16 h / Ambient temperature 3: ethyl acetate / 1.5 h / Ambient temperature 4: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / Ambient temperature 5: NaIO4 / dioxane; H2O / 16 h / Ambient temperature 6: H2 / 20percent Pd(OH)2/C / methanol / 2 h View Scheme