hydrogen; palladium on activated charcoal in ethanol

1: Et3N / dioxane / 0 °C 2: 100 percent / H2 / Pd/C / ethanol View Scheme

1: NEt3 / dioxane; H2O / 4 h / Ambient temperature 2: 78 percent / H2 / 5percent Pd/C / ethanol; H2O / 12 h 3: NEt3 / tetrahydrofuran / 0.5 h / -10 °C 4: NaBH4 / H2O; tetrahydrofuran / 4 h / Ambient temperature 5: 77 percent / CBr4 / PPh3 / tetrahydrofuran / 1) ca.15 deg C, 10 min 2) r.t. View Scheme