1: 1.) Raney nickel, 2.) hydrogen / 2.) palladium on charcoal / 1.) ethanol, reflux, 15 - 20 min, 2.) methanol, 2: 2.5 g / triethylamine / CH2Cl2 / 0.17 h / 0 - 10 °C 3: 1.12 g / aq. hydrochloric acid / tetrahydrofuran / 0.67 h / 18 °C 4: 1.83 g / sodium borohydride / methanol / 0.17 h / Ambient temperature 5: sodium hydroxide / methanol; H2O / 1 h / 70 °C View Scheme

1: 1.) Raney nickel, 2.) hydrogen / 2.) palladium on charcoal / 1.) ethanol, reflux, 15 - 20 min, 2.) methanol, 2: 2.5 g / triethylamine / CH2Cl2 / 0.17 h / 0 - 10 °C 3: 1.12 g / aq. hydrochloric acid / tetrahydrofuran / 0.67 h / 18 °C 4: 1.83 g / sodium borohydride / methanol / 0.17 h / Ambient temperature View Scheme

hydrogen; nickel; palladium on activated charcoal 1.) ethanol, reflux, 15 - 20 min, 2.) methanol,; Yield given. Multistep reaction;