1: With trifluoroacetic acid in dichloromethane T=30°C; 3 h; 2: With sodium hydrogencarbonate in dichloromethane pH=7 - 8;

1.1: 28.0 g / aq. HCl; H2 / Pd/C / methanol / 2 h / 1034.3 Torr 2.1: 98 percent / Et3N / CH2Cl2 / 1 h / -10 °C 3.1: 80 percent / POCl3 / 1 h / 105 °C 4.1: NaBH4 / ethanol / 1 h / 20 °C 4.2: 94 percent / ethanol; acetone / 1 h / Heating 5.1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 6.1: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1.1: NaN3 / acetone / 20 °C 2.1: 28.0 g / aq. HCl; H2 / Pd/C / methanol / 2 h / 1034.3 Torr 3.1: 98 percent / Et3N / CH2Cl2 / 1 h / -10 °C 4.1: 80 percent / POCl3 / 1 h / 105 °C 5.1: NaBH4 / ethanol / 1 h / 20 °C 5.2: 94 percent / ethanol; acetone / 1 h / Heating 6.1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 7.1: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1.1: NaBH4 / ethanol / 1 h / 20 °C 1.2: 94 percent / ethanol; acetone / 1 h / Heating 2.1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 3.1: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 2: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1.1: 80 percent / POCl3 / 1 h / 105 °C 2.1: NaBH4 / ethanol / 1 h / 20 °C 2.2: 94 percent / ethanol; acetone / 1 h / Heating 3.1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 4.1: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1: 81 percent / aq. NaOH / dioxane; acetonitrile / 25 °C 2: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 3: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et3N / dimethylformamide; CH2Cl2 / 1.5 h / 20 °C 2: 13.3 g / HCl / CHCl3; dioxane / 14 h / 45 - 60 °C View Scheme

1.1: sodium azide / acetone / 25 °C 2.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / methanol 3.1: triethylamine / dichloromethane / 1.25 h / -10 - -5 °C 4.1: trichlorophosphate / 1 h / 105 °C 5.1: ethanol; sodium tetrahydroborate / acetone / 1 h / 20 °C 5.2: 1 h / Reflux 6.1: 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 50 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 30 °C 7.2: pH 7 - 8 View Scheme