sodium hydrogencarbonate in methanol; water T=20°C; 24 h;

in tetrahydrofuran 3 h; Reflux;

nitrosyl chloride in formic acid

water

1: sodium azide / N,N-dimethyl-formamide; water / 12 h / 20 °C 2: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -10 °C 3: tetrahydrofuran / 20 °C 4: tributylphosphine; water / dichloromethane / 0.25 h / 20 - 50 °C / |Microwave irradiation View Scheme

1: 1.) Et3N, 2.) hydroxybenzotriazole (HOBt), dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 0.5 h, 2.) CH2Cl2, 16 h 2: 81 percent / ammonia / methanol / 48 h / Ambient temperature View Scheme