ammonium hydroxide T=100°C; 15 h;

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: 65 percent / 25percent aq. NH3 / 15 h / 100 °C 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: 65 percent / 25percent aq. NH3 / 15 h / 100 °C View Scheme

acetic acid 3.25 h; Ambient temperature;

hydrogen; palladium on activated charcoal in ethanol

1: 1) Zn/Cu 2) OH-resin 2: H2 / Pd/C / ethanol View Scheme

1: acetonitrile 2: 1) Zn/Cu 2) OH-resin 3: H2 / Pd/C / ethanol 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: 65 percent / 25percent aq. NH3 / 15 h / 100 °C View Scheme

1: 75 percent / 4-dimethylaminopyridine / acetonitrile / 5 h / Ambient temperature 2: 90 percent / tributyltin hydride, 2,2'-azobis (2-methylpropionitrile) / benzene / 1.33 h / Heating 3: 88 percent / 80percent aq. HOAc / 3.25 h / Ambient temperature View Scheme

1: 90 percent / tributyltin hydride, 2,2'-azobis (2-methylpropionitrile) / benzene / 1.33 h / Heating 2: 88 percent / 80percent aq. HOAc / 3.25 h / Ambient temperature View Scheme