1: palladium 10 on activated carbon; hydrogen / ethanol / 258.58 Torr / Reflux 2: hydrogenchloride / ethanol / 3 h / 40 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / ethanol / 258.58 Torr / Reflux 2: hydrogenchloride / ethanol / 3 h / 40 °C View Scheme

Multi-step reaction with 7 steps 1: Collins reagent / CH2Cl2 / 5 °C2: tetrahydrofuran / 0 °C3: 58 percent / NaBH4 / ethanol; various solvent(s) / 1 h / Heating4: H2, 10percent Pd/C / ethanol / 1551.4 Torr5: 60 percent / ethanol / Heating6: 60 percent / NaBH4 / ethanol; tetrahydrofuran / Heating