1: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 2: 98 percent / 15percent hydrogen fluoride/pyridine mixture / acetonitrile / 1.) 0 deg C; 2.) 24 deg C, 30 min; 3.) 24 deg C, 3 h View Scheme

1: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 2: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 3: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme