hydrogen; platinum in ethanol Ambient temperature;

1: thionyl chloride / dimethylformamide / 1 h / 30 °C 2: 1 h / 20 °C View Scheme

1: 86 percent / pyridine, piperidine / 3 h / 120 °C 2: 70 percent / sodium borohydride / methanol / 1.) 5 deg C, 15 min, 2.) 20 deg C, 0.5 h 3: 2.33 g / TsOH*Py / acetone; H2O / 2 h / Heating 4: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h 5: sodium hydroxide / H2O; methanol / 2 h / Heating 6: quinoline / Heating 7: thionyl chloride / dimethylformamide / 1 h / 30 °C 8: 1 h / 20 °C View Scheme

1: quinoline / Heating 2: thionyl chloride / dimethylformamide / 1 h / 30 °C 3: 1 h / 20 °C View Scheme

1: sodium hydroxide / H2O; methanol / 2 h / Heating 2: quinoline / Heating 3: thionyl chloride / dimethylformamide / 1 h / 30 °C 4: 1 h / 20 °C View Scheme

1: 70 percent / sodium borohydride / methanol / 1.) 5 deg C, 15 min, 2.) 20 deg C, 0.5 h 2: 2.33 g / TsOH*Py / acetone; H2O / 2 h / Heating 3: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h 4: sodium hydroxide / H2O; methanol / 2 h / Heating 5: quinoline / Heating 6: thionyl chloride / dimethylformamide / 1 h / 30 °C 7: 1 h / 20 °C View Scheme

1: 2.33 g / TsOH*Py / acetone; H2O / 2 h / Heating 2: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h 3: sodium hydroxide / H2O; methanol / 2 h / Heating 4: quinoline / Heating 5: thionyl chloride / dimethylformamide / 1 h / 30 °C 6: 1 h / 20 °C View Scheme

T=20°C; 1 h; Yield given;