ammonium hydroxide in tetrahydrofuran T=0°C; 0.5 h; Yield given;

sodium tetrahydroborate in methanol; water T=-15°C; 0.25 h; Inert atmosphere;

1: -5 deg C to room t. 2: 93 percent / H2O / CF3CO2Ag / tetrahydrofuran; triethylamine / 3 h / -25 deg C to room t. View Scheme

hydrazine in tetrahydrofuran; methanol T=0 - 20°C;

in diethyl ether 3 h; Ambient temperature;

1.1: sodium tetrahydroborate / methanol; water / 0.25 h / -15 °C / |Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -78 °C / |Inert atmosphere 2.2: 0.25 h / -78 °C / |Inert atmosphere View Scheme