pyridine; triethylamine in chloroform

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=0 - 20°C;

sodium hydroxide in chloroform T=25°C; 12 h;

1: Et3N / CH2Cl2 / 0.5 h / 0 °C 2: NaN3 / dimethylformamide / 16 h / 80 °C 3: 3.6 g / PPh3; water; aq. HCl / tetrahydrofuran; CH2Cl2 / 16 h / Heating 4: 83 percent / Et3N; DMAP / CH2Cl2 / 16 h / 20 °C View Scheme

1: NaN3 / dimethylformamide / 16 h / 80 °C 2: 3.6 g / PPh3; water; aq. HCl / tetrahydrofuran; CH2Cl2 / 16 h / Heating 3: 83 percent / Et3N; DMAP / CH2Cl2 / 16 h / 20 °C View Scheme

1: 1.) NaBH4, BF3*Et2O, 2.) H2NOSO3H / 1.) DME, ether, 2.) DME, ether, reflux, 4 h 2: 26 percent / aq. NaOH / CHCl3 / 12 h / 25 °C View Scheme

1: 96 percent / MCPBA / CHCl3 / 1 h / Ambient temperature 2: 2percent aq.H2SO4 / 1 h / Ambient temperature 3: pyridine / Ambient temperature 4: 6N HCl / H2O / 24 h / Heating 5: Et3N / butan-1-ol / 48 h / Heating 6: 75.5 percent / AcONa*3H2O, glacial AcOH / H2O / Ambient temperature 7: 65 percent / Zn, AcOH / ethanol; H2O / 5 h / 80 - 85 °C 8: 2.) 0.5N HCl / 1.) 80 deg C, 20 h, 2.) H2O, RT, 30 min 9: 75 percent / 1N HCl / H2O / 5 h / Heating View Scheme

1: 96 percent / MCPBA / CHCl3 / 1 h / Ambient temperature 2: 2percent aq.H2SO4 / 1 h / Ambient temperature 3: pyridine / Ambient temperature 4: 6N HCl / H2O / 24 h / Heating 5: Et3N / butan-1-ol / 48 h / Heating 6: 75.5 percent / AcONa*3H2O, glacial AcOH / H2O / Ambient temperature 7: 65 percent / Zn, AcOH / ethanol; H2O / 5 h / 80 - 85 °C 8: 2.) 0.5N HCl / 1.) 80 deg C, 20 h, 2.) H2O, RT, 30 min 9: 91 percent / NH3 / methanol / 48 h / 100 °C View Scheme