1: 97 percent / N-methylmorpholine, hydroxybenztriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 1.) -12 deg C, 5.5 h, 2.) RT, 16 h 2: H2 / 10percent Pd/C / ethanol / 4 h / 2327.2 Torr 3: 0.67 h / 200 °C 4: lithium aluminum hydride / dioxane / 45 h / 100 °C 5: 1.) N-methylmorpholine / 1.) a) CH2Cl2, 0 deg C, 10 min, b) 20 deg C, 20 min, 2.) H2O, dioxane, 100 deg C, 45 min 6: 42 percent / potassium iodide, sodium carbonate / dimethylformamide / 22.5 h / Ambient temperature View Scheme

sodium carbonate; potassium iodide in N,N-dimethyl-formamide 22.5 h; Ambient temperature;

1: POCl3, Na2CO3 / 60 - 110 °C 2: thiourea / ethanol / Heating View Scheme