1: 68 percent / 4-dimethylaminopyridine / CH2Cl2 / 3 h / 18 °C 2: 98 percent / tributyltin hydride, di-t-butyl peroxide / 0.58 h / 50 °C 3: 87 percent / H2, 5percent Pd/BaSO4, quinoline / benzene; cyclohexane / 4.5 h / 40 °C / 760 Torr 4: 98 percent / hydrogen fluoride, pyridine / 3 h / 24 °C View Scheme

1: 68 percent / 4-dimethylaminopyridine / CH2Cl2 / 3 h / 18 °C 2: 98 percent / tributyltin hydride, di-t-butyl peroxide / 0.58 h / 50 °C 3: 87 percent / H2, 5percent Pd/BaSO4, quinoline / benzene; cyclohexane / 4.5 h / 40 °C / 760 Torr 4: 87 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol 5: 85 percent / acetic acid; H2O; tetrahydrofuran / 1.5 h / 55 °C View Scheme