18-crown-6 ether; potassium carbonate

lithium aluminium tetrahydride in tetrahydrofuran Reduction; 1 h; Heating;

18-crown-6 ether; potassium carbonate in acetone T=70°C; 48 h;

1: 80 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 12 h / Heating 2: 98 percent / LiAlH4 / tetrahydrofuran / 6.5 h / 0 - 20 °C 3: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 4: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 5: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C View Scheme

1: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 2: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 3: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C View Scheme

1: 98 percent / LiAlH4 / tetrahydrofuran / 6.5 h / 0 - 20 °C 2: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 3: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 4: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C View Scheme

diisobutylaluminium hydride in hexane; toluene T=-60 - -10°C; 2 h; Inert atmosphere;

18-crown-6 ether; potassium carbonate in acetone Alkylation; Heating;

1: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 2: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C View Scheme

1.1: 1-methyl-pyrrolidin-2-one / 18 h / 70 °C 2.1: K2CO3 / 1-methyl-pyrrolidin-2-one / 3 h / 140 °C 3.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 120 °C 4.2: 80 percent / KOH / 1-methyl-pyrrolidin-2-one / 3 h / 120 °C View Scheme