1: CuI, (Ph3P)2PdCl2 / diethylamine / Ambient temperature 2: H2 / 5percent Pd-C / ethanol / 3.5 h / 2327.2 Torr 3: 98 percent / p-toluenesulfonic acid monohydrate, EtOH / 3 h / 65 °C 4: triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 18 h 5: 94 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 6: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature 7: 82 percent / NaH / tetrahydrofuran / 120 h 8: 79 percent / Mg(ClO4)2, NaN3 / acetonitrile / 36 h / 75 °C 9: H2 / 5percent Pd-C / tetrahydrofuran / 2 h / 1551.4 - 2327.2 Torr 10: Et3N / CH2Cl2 / 0.5 h View Scheme

triethylamine in dichloromethane 0.5 h;