water; iodine in acetonitrile T=60°C;

lithium hydroxide in tetrahydrofuran T=0°C; 1 h;

1: 92 percent / K2CO3 / dimethylformamide / 9 h / 20 °C 2: 80 percent / lithium chloride; sodium borohydride; ethanol / tetrahydrofuran / 19 h / 20 °C 3: 88 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 4: morpholine / tetrahydrofuran / 10 h / 47 °C View Scheme