ammonium hydroxide; hydrogen; palladium on activated charcoal in methanol 3 h; Ambient temperature;

1: 1.) KOH / 1.) tris-<2-(2-methoxyethoxy)ethyl>amine / 1.) MeCN, room temp., 5 min, 2.) room temp., 15 min 2: 84 percent / NH3 / methanol / 24 h / Ambient temperature 3: 78 percent / pyridine, N,N-diisopropylethylamine / 3 h / Ambient temperature 4: 76 percent / 4-dimethylaminopyridine / acetonitrile / 16 h / Ambient temperature 5: 75 percent / n-Bu3SnH, 2,2'-azobis(2-methyl)propionitrile / toluene / 2 h / 75 °C 6: 67 percent / 80percent aq. AcOH / 0.5 h / Ambient temperature 7: 75 percent / H2, conc. aq. NH3 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme

1: 84 percent / NH3 / methanol / 24 h / Ambient temperature 2: 78 percent / pyridine, N,N-diisopropylethylamine / 3 h / Ambient temperature 3: 76 percent / 4-dimethylaminopyridine / acetonitrile / 16 h / Ambient temperature 4: 75 percent / n-Bu3SnH, 2,2'-azobis(2-methyl)propionitrile / toluene / 2 h / 75 °C 5: 67 percent / 80percent aq. AcOH / 0.5 h / Ambient temperature 6: 75 percent / H2, conc. aq. NH3 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme

1: 1.) KOH / 1.) tris-<2-(2-methoxyethoxy)ethyl>amine / 1.) MeCN, room temp., 5 min, 2.) room temp., 15 min 2: 84 percent / NH3 / methanol / 24 h / Ambient temperature 3: 78 percent / pyridine, N,N-diisopropylethylamine / 3 h / Ambient temperature 4: 76 percent / 4-dimethylaminopyridine / acetonitrile / 16 h / Ambient temperature 5: 75 percent / n-Bu3SnH, 2,2'-azobis(2-methyl)propionitrile / toluene / 2 h / 75 °C 6: 67 percent / 80percent aq. AcOH / 0.5 h / Ambient temperature 7: 75 percent / H2, conc. aq. NH3 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme

1: 67 percent / 80percent aq. AcOH / 0.5 h / Ambient temperature 2: 75 percent / H2, conc. aq. NH3 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme