formic acid; zinc in ethylene glycol T=100 - 120°C; 8 h;

1: With bromine; sodium hydroxide in 1,4-dioxane; water T=5 - 7°C; 3 h; 2: With hydrogenchloride in water TemperatureTime;

formic acid in ethylene glycol T=100 - 105°C; 8 h;

1: potassium carbonate; sodium periodate; potassium permanganate / tert-butyl alcohol; water / 1 h / 50 °C 2: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / |Inert atmosphere 3: ammonium acetate / tetrahydrofuran / 1 h / |Reflux; |Inert atmosphere 4: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 5: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 6: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C View Scheme

1: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / |Inert atmosphere 2: ammonium acetate / tetrahydrofuran / 1 h / |Reflux; |Inert atmosphere 3: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 4: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 5: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C View Scheme

1: ammonia / methanol / 0.5 h / 0 - 25 °C 2: toluene-4-sulfonic acid / methanol / 0.58 h 3: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 4: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C View Scheme

1: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 2: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C View Scheme

1: toluene-4-sulfonic acid / methanol / 0.58 h 2: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 3: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C View Scheme

1: thionyl chloride, pyridine / CH2Cl2 / 1 h 2: CH2Cl2; pyridine / 1 h 3: 40.36 percent / <C6H5Se(O)>2O / chlorobenzene / 10 h / Heating View Scheme

1: 3-oxo-4-aza-5α-androstane-17β-carboxylic acid With 1,1'-carbonyldiimidazole in 1-methyl-pyrrolidin-2-one T=20 - 30°C; 5 h; 2: tert-butylamine With 2-hydroxy-pyridine in 1-methyl-pyrrolidin-2-one T=100°C; P=517.162 - 1034.32 Torr; 6 h;