hydrogenchloride in 1,4-dioxane 4 h; Ambient temperature;

1: N-methylmorpholine / toluene / 16 h / Ambient temperature 2: 64 percent / H2, AcOH / 5percent Pd/C / 5 h / 70 °C / 2280 Torr 3: 69 percent / diphenyl phosphorazidate, N-methylmorpholine / dimethylformamide / 16 h / Ambient temperature 4: 31 percent / 4 N aq. HCl / dioxane / 4 h / Ambient temperature View Scheme

1: 64 percent / H2, AcOH / 5percent Pd/C / 5 h / 70 °C / 2280 Torr 2: 69 percent / diphenyl phosphorazidate, N-methylmorpholine / dimethylformamide / 16 h / Ambient temperature 3: 31 percent / 4 N aq. HCl / dioxane / 4 h / Ambient temperature View Scheme

1: 69 percent / diphenyl phosphorazidate, N-methylmorpholine / dimethylformamide / 16 h / Ambient temperature 2: 31 percent / 4 N aq. HCl / dioxane / 4 h / Ambient temperature View Scheme

1: 84 percent / Et3N / dimethylformamide / 1.5 h / Ambient temperature 2: 98 percent / NaH / dimethylformamide / 1.) 5 deg C to RT, 1 h; 2.) 1 h 3: 81 percent / N-methylmorpholine, tert-butyl hypochlorite / toluene / 1.) from -40- -50 deg C to RT, 3 h; 2.) 2 h 4: 65 percent / Mg / methanol / 4 h / 30 °C 5: 83 percent / 80 percent aq. acetic acid / 0.5 h / 50 °C 6: 96 percent / Et3N / various solvent(s) / 24 h / 50 °C 7: 78 percent / 4 mol dm-3 HCl / dioxane / 16 h / Ambient temperature View Scheme

1: 84 percent / Et3N / dimethylformamide / 1.5 h / Ambient temperature 2: 98 percent / NaH / dimethylformamide / 1.) 5 deg C to RT, 1 h; 2.) 1 h 3: 81 percent / N-methylmorpholine, tert-butyl hypochlorite / toluene / 1.) from -40- -50 deg C to RT, 3 h; 2.) 2 h 4: 65 percent / Mg / methanol / 4 h / 30 °C 5: 83 percent / 80 percent aq. acetic acid / 0.5 h / 50 °C View Scheme