dowex in methanol T=45°C;

1: n-butyllithium / 1.) THF, -78 deg C, 2.) HMPA, room temperature 2: 99 percent / H2, quinoline / Pd/BaSO4 / methanol 3: 90 percent / Dowex / methanol / 45 °C View Scheme

1: 52.9 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 1) -78 deg C, 2) room temperature 2: n-butyllithium / 1.) THF, -78 deg C, 2.) HMPA, room temperature 3: 99 percent / H2, quinoline / Pd/BaSO4 / methanol 4: 90 percent / Dowex / methanol / 45 °C View Scheme

1: 99 percent / H2, quinoline / Pd/BaSO4 / methanol 2: 90 percent / Dowex / methanol / 45 °C View Scheme