in tetrahydrofuran; hexane

1: 85 percent / p-toluenesulfonic acid monohydrate / 1.) 10 min, 100 deg C, 2.) benzene, reflux, 12 h 2: 96 percent / H2 / 10percent Pd/C / methanol / 12 h / 1034.3 Torr 3: 44 percent / NaHCO3 / H2O; ethyl acetate / 1.) 0 deg C, 1.5 h, 2.) RT 4: 82 percent / H2 / 10percent Pd/C / ethanol; H2O / 6 h / 1034.3 Torr 5: CHCl3 / Ambient temperature 6: H2O / acetone View Scheme