1: 76 percent / PBr3, pyridine / diethyl ether / 1 h / Heating 2: 1.) aq. Na2S2O3, 2.) I2 / 1.) THF, reflux, 1.5 h, 2.) reflux, 1 h View Scheme

1: 76 percent / PBr3, pyridine / diethyl ether / 1 h / Heating 2: 1.) aq. Na2S2O3, 2.) I2 / 1.) THF, reflux, 1.5 h, 2.) reflux, 1 h 3: 89 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1 h / 0 - 25 °C View Scheme

lithium aluminium tetrahydride in diethyl ether 1a.) -20 deg C, 0.5 h, b.) from -20 deg C to RT, 1 h;

n-butyllithium; diisobutylaluminium hydride in tetrahydrofuran; hexane

1: 96 percent / LiAlH4 / diethyl ether / 0.75 h / -20 °C 2: 92 percent / LiAlH4 / diethyl ether / 1a.) -20 deg C, 0.5 h, b.) from -20 deg C to RT, 1 h View Scheme

1: 89 percent / N,N'-dibromodimethylhydantoin / CCl4 / 12 h / 50 - 60 °C 2: 80 percent / AgClO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 3: 92 percent / HCl / CHCl3 / 1 h / Ambient temperature 4: 90 percent / LiAlH4 View Scheme

1: 92 percent / HCl / CHCl3 / 1 h / Ambient temperature 2: 90 percent / LiAlH4 View Scheme

1: 87 percent / TiCl4, Zn / tetrahydrofuran / 24 h / 50 - 60 °C 2: 89 percent / N,N'-dibromodimethylhydantoin / CCl4 / 12 h / 50 - 60 °C 3: 80 percent / AgClO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 4: 92 percent / HCl / CHCl3 / 1 h / Ambient temperature 5: 90 percent / LiAlH4 View Scheme

1: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1.5 h / 0 - 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran / 3 h View Scheme