hydrogen; palladium on activated charcoal in ethanol Yield given;

1: 12.93 g / methanol; dioxane / 2.5 h / Heating 2: 1.) H2, semicarbazide hydrochloride, NaOAc, 2.) 10percent aq. HCl, 36percent aq. CH2O / 1.) Raney Ni / 1.) EtOH, H2O, 50 psi, 2.) EtOH, H2O, heating, 30 min 3: pyridine, piperidine / Heating 4: H2 / 5percent Pd/C / ethanol View Scheme

1: 1.) H2, semicarbazide hydrochloride, NaOAc, 2.) 10percent aq. HCl, 36percent aq. CH2O / 1.) Raney Ni / 1.) EtOH, H2O, 50 psi, 2.) EtOH, H2O, heating, 30 min 2: pyridine, piperidine / Heating 3: H2 / 5percent Pd/C / ethanol View Scheme

1: pyridine, piperidine / Heating 2: H2 / 5percent Pd/C / ethanol View Scheme