1: 97 percent / LiAlH4 / diethyl ether / 12 h / 25 °C 2: 93 percent / celite / benzene / 4 h / porcine pancreatic lipase 3: 93 percent / triethylamine / tetrahydrofuran / 3 h / 0 - 25 °C 4: 84 percent / dimethylsulfoxide / 12 h / 45 °C 5: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 6: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 7: 82 percent / NaN3 / dimethylformamide / 40 °C 8: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 9: 6 N aq. HCl / 18 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether T=25°C; 12 h;