in methanol T=20°C; 24 h;

1: 99 percent / methanol / 1.5 h / Heating 2: H2 / Pd/C / methanol / 17 h 3: 27 percent / AcOH / CH2Cl2 / 72 h / 20 °C 4: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 5: 84 percent / 3-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 6: 83 percent / conc. HCl / 1.33 h / 90 °C 7: Et3N / acetone / 0.25 h / 0 °C 8: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 9: 60 percent / methanol / 24 h / 20 °C View Scheme

1: H2 / Pd/C / methanol / 17 h 2: 27 percent / AcOH / CH2Cl2 / 72 h / 20 °C 3: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 4: 84 percent / 3-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 5: 83 percent / conc. HCl / 1.33 h / 90 °C 6: Et3N / acetone / 0.25 h / 0 °C 7: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 8: 60 percent / methanol / 24 h / 20 °C View Scheme

1: 99 percent / methanol / 1.5 h / Heating 2: H2 / Pd/C / methanol / 17 h 3: 27 percent / AcOH / CH2Cl2 / 72 h / 20 °C 4: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 5: 84 percent / 3-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 6: 83 percent / conc. HCl / 1.33 h / 90 °C 7: Et3N / acetone / 0.25 h / 0 °C 8: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 9: 60 percent / methanol / 24 h / 20 °C View Scheme

1: 27 percent / AcOH / CH2Cl2 / 72 h / 20 °C 2: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 3: 84 percent / 3-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 4: 83 percent / conc. HCl / 1.33 h / 90 °C 5: Et3N / acetone / 0.25 h / 0 °C 6: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 7: 60 percent / methanol / 24 h / 20 °C View Scheme

1: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 2: 84 percent / 3-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 3: 83 percent / conc. HCl / 1.33 h / 90 °C 4: Et3N / acetone / 0.25 h / 0 °C 5: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 6: 60 percent / methanol / 24 h / 20 °C View Scheme

1: Et3N / acetone / 0.25 h / 0 °C 2: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 3: 60 percent / methanol / 24 h / 20 °C View Scheme