hydrogen; palladium on activated charcoal in methanol 16 h;

1: 85 percent / p-toluenesulphonic acid / acetonitrile 2: 86 percent / sodium hydride / 1,2-dimethoxy-ethane 3: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 4: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight 5: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 6: 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 View Scheme

1: 86 percent / sodium hydride / 1,2-dimethoxy-ethane 2: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 3: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight 4: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 5: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h View Scheme

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

1: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 2: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h View Scheme

1: 95 percent / silver zeolite / CH2Cl2 / 1 h / Ambient temperature 2: 85 percent / sodium methoxide / methanol 3: 85 percent / p-toluenesulphonic acid / acetonitrile 4: 86 percent / sodium hydride / 1,2-dimethoxy-ethane 5: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 6: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight 7: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 8: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h View Scheme

1: 85 percent / sodium methoxide / methanol 2: 85 percent / p-toluenesulphonic acid / acetonitrile 3: 86 percent / sodium hydride / 1,2-dimethoxy-ethane 4: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 5: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight 6: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight 7: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h View Scheme

1: 65 percent / tetraethylammonium bromide, molecular sieves / CH2Cl2; dimethylformamide / 16 h / Ambient temperature 2: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol View Scheme