hydrogenchloride in water T=45°C; deprotection;

1: 80 percent / H2O2; NaOH / methanol / 0.83 h / -40 °C 2: 91 percent / NaH / tetrahydrofuran / 1 h / 20 °C 3: 77 percent / NH3 / ethanol / 3 h / 20 °C 4: NaHCO3 / ethyl acetate; H2O / 20 °C 5: 77 percent / hydrogen / 10 percent Pd/C / ethanol 6: 27 percent / HCl / H2O / 45 °C View Scheme

1: 91 percent / NaH / tetrahydrofuran / 1 h / 20 °C 2: 77 percent / NH3 / ethanol / 3 h / 20 °C 3: NaHCO3 / ethyl acetate; H2O / 20 °C 4: 77 percent / hydrogen / 10 percent Pd/C / ethanol 5: 27 percent / HCl / H2O / 45 °C View Scheme

1: 77 percent / NH3 / ethanol / 3 h / 20 °C 2: NaHCO3 / ethyl acetate; H2O / 20 °C 3: 77 percent / hydrogen / 10 percent Pd/C / ethanol 4: 27 percent / HCl / H2O / 45 °C View Scheme

1: NaHCO3 / ethyl acetate; H2O / 20 °C 2: 77 percent / hydrogen / 10 percent Pd/C / ethanol 3: 27 percent / HCl / H2O / 45 °C View Scheme

1: 77 percent / hydrogen / 10 percent Pd/C / ethanol 2: 27 percent / HCl / H2O / 45 °C View Scheme

1: 88 percent / H2 / 10 percent Pd/C / ethanol 2: 27 percent / HCl / H2O / 45 °C View Scheme