lithium aluminium tetrahydride in tetrahydrofuran 72 h; Reflux;

lithium aluminium tetrahydride in diethyl ether T=0 - 20°C;

1: in dichloromethane T=0°C; 5 h; 2: With potassium fluoride; water in dichloromethane T=25°C; 0.5 h;

1,4-diaza-bicyclo[2.2.2]octane; sodium tetrahydroborate; sodium sulfate 1.) THF, RT, 48 h, 2.) EtOH, RT, 48 h; Multistep reaction. Title compound not separated from byproducts;

1: Novozym 435 / various solvent(s) / 6.5 h / 0 °C 2: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0 - 20 °C 3: NaClO2; amylene; NaH2PO4*2H2O / tetrahydrofuran; H2O / 4 h 4: triethylamine; diphenylphosphoryl azide / toluene / 6 h / Heating 5: 14 h / 100 °C 6: H2O; K2CO3 / methanol / 2 h View Scheme