benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine in dichloromethane T=20°C; 72 h;

1: 97 percent / TEA / methanol / a) 50 deg C, 5 min, b) RT, 1 h 2: 93 percent / TEA, BOP / CH2Cl2 / 6 h View Scheme

1: 97 percent / TEA / methanol / a) 50 deg C, 5 min, b) RT, 1 h 2: 93 percent / TEA, BOP / CH2Cl2 / 6 h View Scheme

1: With lithium aluminium tetrahydride in diethyl ether T=0 - 20°C; 0.5 h; 2: With potassium hydrogensulfate in diethyl ether; water T=0°C;

1.1: diisobutylaluminium hydride / dichloromethane / -78 °C / |Inert atmosphere 1.2: 0 - 20 °C 2.1: hydrogenchloride / water; diethyl ether / |Reflux 2.2: 0 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0); diisopropylamine; copper(l) iodide 4.1: mercury(II) oxide; mercury(II) trifluoroacetate; water / tetrahydrofuran / 1 h / 0 °C 5.1: diisopropylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / 70 °C / |Inert atmosphere 6.1: 1,4-dioxane / 23 h / |Inert atmosphere; |Reflux 6.2: 48 h / |Reflux 7.1: trifluoromethylsulfonic anhydride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 0 - 20 °C / |Inert atmosphere 7.2: 3 h / |Reflux View Scheme