1: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight 2: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 3: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h View Scheme

1: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight 2: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 3: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h 4: 65 percent / tetraethylammonium bromide, molecular sieves / CH2Cl2; dimethylformamide / 16 h / Ambient temperature 5: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol View Scheme