18-crown-6 ether; tert-butylamine in tetrahydrofuran Ambient temperature;

1: 12 percent / K, 18-crown-6, t-BuNH2 / tetrahydrofuran / Ambient temperature 2: 70 percent / sodium hydride, iodomethane / tetrahydrofuran / 16 h / 23 °C 3: 74 percent / K, 18-crown-6 / tetrahydrofuran; 1,2-dimethoxy-ethane / Ambient temperature View Scheme

18-crown-6 ether; tert-butylamine in tetrahydrofuran Ambient temperature;

1: 5 percent / K, 18-crown-6, t-BuNH2 / tetrahydrofuran / Ambient temperature 2: 100 percent / pyridine / CHCl3 / 17 h / 23 °C 3: 63 percent / pyridine / 24 h / 23 °C 4: 66 percent / Li, EtNH2 / Ambient temperature; further reagent 5: 78 percent / n-butyl-lithium, iodomethane / tetrahydrofuran / 2 h / 23 °C 6: 68 percent / Li, EtNH2 / Ambient temperature; further reagent 7: 53 percent / n-butyl-lithium / tetrahydrofuran; hexane / 1 h / -20 °C 8: 19 percent / K, 18-crown-6, t-BuNH2 / tetrahydrofuran / Ambient temperature View Scheme

1: 5 percent / K, 18-crown-6, t-BuNH2 / tetrahydrofuran / Ambient temperature 2: 100 percent / pyridine / CHCl3 / 17 h / 23 °C 3: 31 percent / pyridine / 24 h / 23 °C View Scheme