Multi-step reaction with 7 steps
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
5: NaH / 1,2-dimethoxy-ethane / 20 h / Ambient temperature
6: 59 percent / NaOCH3 / methanol / 18 h / Heating
7: 87 percent / ethanol / 24 h / Heating
With
piperidine; pyridine; hydrogenchloride; formaldehyd; hydrogen; sodium methylate; semicarbazide hydrochloride; sodium acetate; sodium hydride;
palladium on activated charcoal; nickel;
In
1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol;
DOI:10.1016/0223-5234(93)90091-R