1: sodium azide / dimethylformamide / 12 h / 50 °C 2: 1.) PPh3, 2.) H2O / 1.) THF, RT, 12 h, 2.) RT, 12 h View Scheme

sodium hydroxide in tetrahydrofuran; water T=0°C; 8 h; Inert atmosphere;

1: KOH / tetrahydrofuran / 2 h 2: pyridine / 3 h / cooling View Scheme

1: 47.4 g / NaH / paraffin; tetrahydrofuran / 1.) room temperature, 1.5 h, 2.) reflux, 24 h 2: 58 percent / conc. HCl, MeOH / CH2Cl2 / 3 h / Heating 3: 92 percent / triethylbenzylammonium chloride, 30percent aq. NaOH / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 58 percent / conc. HCl, MeOH / CH2Cl2 / 3 h / Heating 2: 92 percent / triethylbenzylammonium chloride, 30percent aq. NaOH / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: aq. NaOH 2: 97 percent / H2 / Pd 3: pyridine (py) View Scheme

1: 97 percent / H2 / Pd 2: pyridine (py) View Scheme