formic acid in tetrahydrofuran; 1,4-dioxane; methanol

hydrogen in methanol 18 h;

ammonia; sodium in tetrahydrofuran T=-78°C; 0.333333 h; Inert atmosphere;

Yield given. Multistep reaction;

1: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature 2: 79 percent / H2 / Pd-black / H2O / 1 h View Scheme

1: 93 percent / pyridine / -40 °C 2: 94 percent / pyridine / 3 h / Ambient temperature 3: 2.2 g / 1M methanolic ammonia / 6 h / Ambient temperature 4: 68 percent / sodium azide, ammonium chloride / dimethylformamide / 1.2 h / Heating 5: 1.) 1.4 M methanolic hydrochloric acid / 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight 6: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature 7: 79 percent / H2 / Pd-black / H2O / 1 h View Scheme

1: 94 percent / pyridine / 3 h / Ambient temperature 2: 2.2 g / 1M methanolic ammonia / 6 h / Ambient temperature 3: 68 percent / sodium azide, ammonium chloride / dimethylformamide / 1.2 h / Heating 4: 1.) 1.4 M methanolic hydrochloric acid / 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight 5: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature 6: 79 percent / H2 / Pd-black / H2O / 1 h View Scheme

1: 2.2 g / 1M methanolic ammonia / 6 h / Ambient temperature 2: 68 percent / sodium azide, ammonium chloride / dimethylformamide / 1.2 h / Heating 3: 1.) 1.4 M methanolic hydrochloric acid / 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight 4: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature 5: 79 percent / H2 / Pd-black / H2O / 1 h View Scheme

1: 68 percent / sodium azide, ammonium chloride / dimethylformamide / 1.2 h / Heating 2: 1.) 1.4 M methanolic hydrochloric acid / 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight 3: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature 4: 79 percent / H2 / Pd-black / H2O / 1 h View Scheme

1: 1.) 1.4 M methanolic hydrochloric acid / 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight 2: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature 3: 79 percent / H2 / Pd-black / H2O / 1 h View Scheme