sodium hydroxide in ethanol; water T=20°C; 1 h;

1: 90 percent / DIEA / dimethylformamide / 4 h / 20 °C 2: 87 percent / pyridine / ethanol / 2 h / Heating 3: 80 percent / BH3*THF / tetrahydrofuran / 3.5 h / Heating 4: 75 percent / sodium cyanoborohydride; HCl / methanol / 24 h / 20 °C 5: HF; anisole / 1 h / 0 °C 6: 505 mg / NaOH / H2O; ethanol / 1 h / 20 °C View Scheme

1: 87 percent / pyridine / ethanol / 2 h / Heating 2: 80 percent / BH3*THF / tetrahydrofuran / 3.5 h / Heating 3: 75 percent / sodium cyanoborohydride; HCl / methanol / 24 h / 20 °C 4: HF; anisole / 1 h / 0 °C 5: 505 mg / NaOH / H2O; ethanol / 1 h / 20 °C View Scheme

1: 80 percent / BH3*THF / tetrahydrofuran / 3.5 h / Heating 2: 75 percent / sodium cyanoborohydride; HCl / methanol / 24 h / 20 °C 3: HF; anisole / 1 h / 0 °C 4: 505 mg / NaOH / H2O; ethanol / 1 h / 20 °C View Scheme

1: 75 percent / sodium cyanoborohydride; HCl / methanol / 24 h / 20 °C 2: HF; anisole / 1 h / 0 °C 3: 505 mg / NaOH / H2O; ethanol / 1 h / 20 °C View Scheme

1: HF; anisole / 1 h / 0 °C 2: 505 mg / NaOH / H2O; ethanol / 1 h / 20 °C View Scheme

1: 97 percent / NaOH / dioxane; H2O / 17 h / 20 °C 2: HF; anisole / 1 h / 0 °C 3: 505 mg / NaOH / H2O; ethanol / 1 h / 20 °C View Scheme