1: 92 percent / LAH / tetrahydrofuran / 0 °C 2: 90 percent / sat. aq. SO2 / 35 - 40 °C 3: 75 percent / hydrogen, Ba(OH)2*8H2O / Raney-Ni / H2O View Scheme

1: 97 percent / LDA / tetrahydrofuran / 2.5 h / -78 °C 2: 79 percent / H2 / PtO2 / ethyl acetate / 20 h / 2327.2 - 2585.7 Torr / other reagent NaBH4 3: CH2Cl2; H2O / a.) 0 to 5 deg C, 2h; b.) 25 deg C, 6h 4: Dowex 1X2 (OH-) resin / H2O 5: 75 percent / LAH / tetrahydrofuran / 20 h / Heating 6: 90percent CF3CO2H / 20 h / 25 °C 7: H2 / 5percent Pt on C / H2O / 20 h / 2585.7 Torr View Scheme