1: With hydrogenchloride; tert.-butylnitrite in tetrahydrofuran T=0°C; 1 h; 2: With sodium azide in tetrahydrofuran; water T=0 - 20°C;

1.1: 46 percent / ammonium formate; Pd/C / dimethylformamide / 16 h / 20 °C 2.1: aq. HCl; t-BuONO / tetrahydrofuran / 1 h / 0 °C 2.2: 85 percent / NaN3 / tetrahydrofuran; H2O / 0 - 20 °C View Scheme

1.1: 97 percent / 16 h / 50 °C 2.1: 82 percent / methanol / 0 - 20 °C 3.1: 46 percent / ammonium formate; Pd/C / dimethylformamide / 16 h / 20 °C 4.1: aq. HCl; t-BuONO / tetrahydrofuran / 1 h / 0 °C 4.2: 85 percent / NaN3 / tetrahydrofuran; H2O / 0 - 20 °C View Scheme