1: H2 / 10percent Pd-C / ethanol / 9.5 h / 80 °C 2: 81 percent / 2 h / 100 °C 3: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 4: 53 percent / aq. HCl / dioxane / 2.5 h / Heating 5: 1.) Li 2.) 10percent Pd-C / 1.) liq. NH3-THF, 35 min 2.) tetralin, 210 deg C, 2 h View Scheme

1: H2 / 10percent Pd-C / ethanol / 9.5 h / 80 °C 2: 81 percent / 2 h / 100 °C 3: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 4: 53 percent / aq. HCl / dioxane / 2.5 h / Heating View Scheme