sodium hydroxide T=20°C; 6 h;

1: 1.) HNO3, <2H2>sulfuric acid, 2.) sodium dichromate, H2SO4 / 1.) D2O, 1.5 h, 2.) H2O, reflux, 5 h 2: 2.43 g / PCl5 / 0.25 h / 60 °C 3: 2.39 g / triethylamine / benzene / 0.25 h / Ambient temperature 4: 0.862 g / H2 / 10percent Pd/C / ethanol / 1 h 5: 262 mg / 0.25 h / 120 - 125 °C / 0.01 Torr 6: 118 mg / sodium borohydride / ethanol / 45 °C 7: 81 mg / NaOH / 80 °C View Scheme

1: 2.43 g / PCl5 / 0.25 h / 60 °C 2: 2.39 g / triethylamine / benzene / 0.25 h / Ambient temperature 3: 0.862 g / H2 / 10percent Pd/C / ethanol / 1 h 4: 262 mg / 0.25 h / 120 - 125 °C / 0.01 Torr 5: 118 mg / sodium borohydride / ethanol / 45 °C 6: 81 mg / NaOH / 80 °C View Scheme

1: 2.39 g / triethylamine / benzene / 0.25 h / Ambient temperature 2: 0.862 g / H2 / 10percent Pd/C / ethanol / 1 h 3: 262 mg / 0.25 h / 120 - 125 °C / 0.01 Torr 4: 118 mg / sodium borohydride / ethanol / 45 °C 5: 81 mg / NaOH / 80 °C View Scheme

1: 0.862 g / H2 / 10percent Pd/C / ethanol / 1 h 2: 262 mg / 0.25 h / 120 - 125 °C / 0.01 Torr 3: 118 mg / sodium borohydride / ethanol / 45 °C 4: 81 mg / NaOH / 80 °C View Scheme

1.1: dicyclohexylcarbodiimide; 1-hydroxybenzotriazole / tetrahydrofuran / 0.5 h / 20 °C 1.2: diisopropylethylamine / tetrahydrofuran / 4 h / 20 °C 2.1: 76 percent / aq. NaOH / methanol / 1.75 h / 20 °C 3.1: 35 percent / glacial acetic acid; dimethylaminoborane / 0.33 h / 60 °C 4.1: 80 percent / aq. NaOH / 6 h / 20 °C View Scheme

1.1: 58.1 percent / deuterium oxide; Pd/C / 2 h / 200 °C 2.1: 2 h / 20 °C 3.1: dicyclohexylcarbodiimide; 1-hydroxybenzotriazole / tetrahydrofuran / 0.5 h / 20 °C 3.2: diisopropylethylamine / tetrahydrofuran / 4 h / 20 °C 4.1: 76 percent / aq. NaOH / methanol / 1.75 h / 20 °C 5.1: 35 percent / glacial acetic acid; dimethylaminoborane / 0.33 h / 60 °C 6.1: 80 percent / aq. NaOH / 6 h / 20 °C View Scheme

1: 86.5 percent / MeONa / methanol / 18 h / 70 °C 2: 92.1 percent / 5 percent aq. NaOH / 0.17 h / Heating 3: 100 percent / aq. formic acid / 0.5 h / 20 °C 4: 69 percent / 10 h / 100 °C 5: 35 percent / glacial acetic acid; dimethylaminoborane / 0.33 h / 60 °C 6: 80 percent / aq. NaOH / 6 h / 20 °C View Scheme

1.1: 2 h / 20 °C 2.1: dicyclohexylcarbodiimide; 1-hydroxybenzotriazole / tetrahydrofuran / 0.5 h / 20 °C 2.2: diisopropylethylamine / tetrahydrofuran / 4 h / 20 °C 3.1: 76 percent / aq. NaOH / methanol / 1.75 h / 20 °C 4.1: 35 percent / glacial acetic acid; dimethylaminoborane / 0.33 h / 60 °C 5.1: 80 percent / aq. NaOH / 6 h / 20 °C View Scheme

1.1: dicyclohexylcarbodiimide; 1-hydroxybenzotriazole / tetrahydrofuran / 0.5 h / 20 °C 1.2: diisopropylethylamine / tetrahydrofuran / 4 h / 20 °C 2.1: 76 percent / aq. NaOH / methanol / 1.75 h / 20 °C 3.1: 35 percent / glacial acetic acid; dimethylaminoborane / 0.33 h / 60 °C 4.1: 80 percent / aq. NaOH / 6 h / 20 °C View Scheme