sodium tetrahydroborate; palladium 10 on activated carbon in methanol; water T=20°C; Inert atmosphere;

sulfuric acid T=95°C; 2 h;

1.1: 79 percent / H2O / 0.25 h / 50 °C 2.1: 1-hydroxybenzotriazole; N,N'-dicyclohexylcarbodiimide / dimethylformamide / 0.5 h / 0 °C 2.2: 86 percent / dimethylformamide / 0 - 20 °C 3.1: 80 percent / NaOiPr / propan-2-ol / Heating 4.1: 90 percent / aq. H2SO4 / 2 h / 95 °C View Scheme

1: 80 percent / NaOiPr / propan-2-ol / Heating 2: 90 percent / aq. H2SO4 / 2 h / 95 °C View Scheme

1.1: 1-hydroxybenzotriazole; N,N'-dicyclohexylcarbodiimide / dimethylformamide / 0.5 h / 0 °C 1.2: 86 percent / dimethylformamide / 0 - 20 °C 2.1: 80 percent / NaOiPr / propan-2-ol / Heating 3.1: 90 percent / aq. H2SO4 / 2 h / 95 °C View Scheme

1.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 3.1: sodium hydride / 1,4-dioxane; mineral oil / 2 h / 70 °C / Cooling with ice; Inert atmosphere 3.2: 4 h / 70 °C / Inert atmosphere 4.1: sodium tetrahydroborate; palladium 10 on activated carbon / methanol; water / 20 °C / Inert atmosphere View Scheme

1.1: sodium hydride / 1,4-dioxane; mineral oil / 2 h / 70 °C / Cooling with ice; Inert atmosphere 1.2: 4 h / 70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; palladium 10 on activated carbon / methanol; water / 20 °C / Inert atmosphere View Scheme