lithium aluminium tetrahydride in diethyl ether 1.66667 h; Ambient temperature;

1: 79 percent / 3-chloroperbenzoic acid / CH2Cl2 / 3 h / Ambient temperature 2: 83 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 3: 59 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 3 h / 750.06 Torr / Ambient temperature 4: 98 percent / LiAlH4 / diethyl ether / 1.67 h / Ambient temperature View Scheme

1: 83 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 2: 59 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 3 h / 750.06 Torr / Ambient temperature 3: 98 percent / LiAlH4 / diethyl ether / 1.67 h / Ambient temperature View Scheme

1: 1.) BuLi / 1.) Et2O, hexane, r.t., 1 h, 2.) r.t., 4 h 2: 79 percent / 3-chloroperbenzoic acid / CH2Cl2 / 3 h / Ambient temperature 3: 83 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 4: 59 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 3 h / 750.06 Torr / Ambient temperature 5: 98 percent / LiAlH4 / diethyl ether / 1.67 h / Ambient temperature View Scheme

1: 59 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 3 h / 750.06 Torr / Ambient temperature 2: 98 percent / LiAlH4 / diethyl ether / 1.67 h / Ambient temperature View Scheme