sodium azide in acetone 24 h; Ambient temperature;

1: 65 percent / Ph3PBr2 / CH2Cl2 / 1 h / Ambient temperature 2: 84 percent / NaN3 / acetone / 24 h / Ambient temperature View Scheme

1: 60 percent / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 65 percent / Ph3PBr2 / CH2Cl2 / 1 h / Ambient temperature 3: 84 percent / NaN3 / acetone / 24 h / Ambient temperature View Scheme

1: 74 percent / NH2OH*HCl / ethanol / 2 h / Heating 2: 60 percent / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 3: 65 percent / Ph3PBr2 / CH2Cl2 / 1 h / Ambient temperature 4: 84 percent / NaN3 / acetone / 24 h / Ambient temperature View Scheme

sodium tetrahydroborate; sodium borohydride; triethylamine in isopropyl alcohol; citric acid

sodium tetrahydroborate; TEA; 1,3-dimercaptopropane in isopropyl alcohol 24 h; Ambient temperature;