lithium aluminium tetrahydride in tetrahydrofuran 18 h; Heating;

1: 94 percent / Et3N / CH2Cl2 / 1.) -75 deg C, 1 h, 2.) -> r.t. 2: 69 percent / H2 / 10percent Pd-C / acetic acid / 1 h / 2068.6 Torr / Ambient temperature 3: 82 percent / NaHCO3 / CH2Cl2 / 3 h / 0 °C 4: 52 percent / ethanol / 1 h / 0 °C 5: 58 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 69 percent / H2 / 10percent Pd-C / acetic acid / 1 h / 2068.6 Torr / Ambient temperature 2: 82 percent / NaHCO3 / CH2Cl2 / 3 h / 0 °C 3: 52 percent / ethanol / 1 h / 0 °C 4: 58 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 1.) 1-chloroethyl carbonochloridate, 2.) MeOH / 1.) 1,2-dichloroethane, a) 0 deg C, 15 min., b) reflux, 1 h, 2.) reflux, 1 h 2: 94 percent / Et3N / CH2Cl2 / 1.) -75 deg C, 1 h, 2.) -> r.t. 3: 69 percent / H2 / 10percent Pd-C / acetic acid / 1 h / 2068.6 Torr / Ambient temperature 4: 82 percent / NaHCO3 / CH2Cl2 / 3 h / 0 °C 5: 52 percent / ethanol / 1 h / 0 °C 6: 58 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 82 percent / NaHCO3 / CH2Cl2 / 3 h / 0 °C 2: 52 percent / ethanol / 1 h / 0 °C 3: 58 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 52 percent / ethanol / 1 h / 0 °C 2: 58 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme