lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1.5 h;

triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran; toluene 2 h; Heating;

1: 97 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 °C 2: 89 percent / PDC; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C 3: 3.82 g / diethyl ether / 1.5 h / -78 °C 4: 81 percent / 2,6-lutidine / CH2Cl2 / 0.08 h / 0 °C 5: 77 percent / aq. CAN / acetonitrile / 0.25 h / 0 °C View Scheme

1: 97 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 °C 2: 89 percent / PDC; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C View Scheme