1: 73 percent / sodium methoxide, hydroxylamine hydrochloride / methanol; tetrahydrofuran / 18 h / 25 °C 2: 84 percent / crown-18 ether / acetonitrile / 4 h / 25 °C 3: 45 percent / hydrazine / ethanol / 72 h / 25 °C 4: 56 percent / N-methyl morpholine / methanol / 4 h / Heating 5: 83.5 percent / 1 N HCl / trifluoroacetic acid / 55 °C 6: 42 percent / sodium dithionite / dimethylformamide / 0.25 h / 50 °C 7: dimethylformamide / 2 h / 100 - 120 °C View Scheme

1: 73 percent / sodium methoxide, hydroxylamine hydrochloride / methanol; tetrahydrofuran / 18 h / 25 °C 2: 84 percent / crown-18 ether / acetonitrile / 4 h / 25 °C 3: 45 percent / hydrazine / ethanol / 72 h / 25 °C 4: 56 percent / N-methyl morpholine / methanol / 4 h / Heating 5: 83.5 percent / 1 N HCl / trifluoroacetic acid / 55 °C 6: 42 percent / sodium dithionite / dimethylformamide / 0.25 h / 50 °C 7: dimethylformamide / 2 h / 100 - 120 °C 8: 33 percent / 1 N NaOH / H2O / 0.5 h / 80 °C 9: thionyl chloride / benzene / 2 h / Heating 10: 2.) HCl / 1.) ether, methylene chloride, RT, 1 h View Scheme

1: 82 percent / sodium azide, potassium iodide / acetone / 2 h 2: 82 percent / p-toluenesulfonic acid monohydrate / benzene / 6 h / Heating 3: 93.5 percent / 0.5 N NaOH / acetonitrile / 18 h / Ambient temperature 4: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h 5: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 6: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 7: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 8: sodium dithionite / dimethylformamide; H2O / 0.5 h 9: 0.1N NaOH / 1.5 h 10: Me2SO / dimethylformamide / 47 h 11: 0.1N NaOH / acetonitrile View Scheme