1: 86 percent / sodium hydride / 1,2-dimethoxy-ethane 2: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 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: 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 6: 65 percent / tetraethylammonium bromide, molecular sieves / CH2Cl2; dimethylformamide / 16 h / Ambient temperature 7: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol View Scheme

1: 86 percent / sodium hydride / 1,2-dimethoxy-ethane 2: 88 percent / 60percent aqueous acetic acid / 0.5 h / 100 °C 3: 42 percent / tetraethylammonium bromide, molecular sieves / CH2Cl2 / 6 h / Ambient temperature View Scheme