in methanol T=20°C; 24 h;

1: 75 percent / H2 / Pd/C / methanol 2: 61 percent / KOH, H2O / 1.25 h / Heating 3: 87 percent / H2SO4 4: 38 percent / acetic acid; tetrahydrofuran / 168 h / 20 °C 5: Et3N / CH2Cl2 / 3 h / 20 °C 6: NaCl / dimethylformamide / 0.08 h / Heating 7: conc. HCl / 1 h / 80 °C 8: Et3N / acetone / 0.25 h / 0 °C 9: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg, 30 min, 2.) reflux, 10 min 10: 74 percent / methanol / 24 h / 20 °C View Scheme

1: 87 percent / H2SO4 2: 38 percent / acetic acid; tetrahydrofuran / 168 h / 20 °C 3: Et3N / CH2Cl2 / 3 h / 20 °C 4: NaCl / dimethylformamide / 0.08 h / Heating 5: conc. HCl / 1 h / 80 °C 6: Et3N / acetone / 0.25 h / 0 °C 7: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg, 30 min, 2.) reflux, 10 min 8: 74 percent / methanol / 24 h / 20 °C View Scheme

1: 61 percent / KOH, H2O / 1.25 h / Heating 2: 87 percent / H2SO4 3: 38 percent / acetic acid; tetrahydrofuran / 168 h / 20 °C 4: Et3N / CH2Cl2 / 3 h / 20 °C 5: NaCl / dimethylformamide / 0.08 h / Heating 6: conc. HCl / 1 h / 80 °C 7: Et3N / acetone / 0.25 h / 0 °C 8: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg, 30 min, 2.) reflux, 10 min 9: 74 percent / methanol / 24 h / 20 °C View Scheme