1: triethylamine / CH2Cl2 / 1 h / -5 °C 2: sodium iodide / acetone / 2 h / 50 °C 3: 1.) sodium amide / 1.) Et2O, liquid NH3, -50 deg C to -40 deg C, 60 min., 2.) -50 deg C to -40 deg C, 100 min. 4: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 5: triethylamine / CH2Cl2 / 1 h / -5 °C 6: sodium iodide / acetone / 2 h / 50 °C 7: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 8: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 9: 91 percent / pyridine-2,6-dicarboxylic acid, cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 - 2 °C View Scheme

1: triethylamine / CH2Cl2 / 1 h / -5 °C 2: sodium iodide / acetone / 2 h / 50 °C View Scheme