1: 18 percent / KOH, tris<2-(2-methoxyethoxy)ethyl>amine / acetonitrile; tetrahydrofuran / 0.17 h / Ambient temperature 2: 66 percent / Bu4NF / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 1.) KOH, tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1) / 1.) MeCN, r.t., 2.) THF, 10 min. 2: 93 percent / Bu4NF / tetrahydrofuran / 0.25 h / Ambient temperature 3: 1,) hydrazine hydrate, 2.) Raney-Ni / 1.) 120-130 deg C, 90 min., 2.) ethanol, 2 h, heating View Scheme

1: 1) tris<2-(2-methoxyethoxy)ethyl>amine, K2CO3 / 1) acetonitrile, room temp., 50 min; 2) acetonitrile, room temp., 60 min 2: 72 percent / Raney-Ni / methanol; dioxane / Ambient temperature 3: 85 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 4: 1) POCl3; 2) (Bu3NH)4P2O7, Bu3N / 1) PO(OMe)3, 4 deg C, 3 h; 2) DMF, 0 deg C, 1 min View Scheme

1: 1) tris<2-(2-methoxyethoxy)ethyl>amine, K2CO3 / 1) acetonitrile, room temp., 50 min; 2) acetonitrile, room temp., 60 min 2: 79 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 3: 1) POCl3; 2) (Bu3NH)4P2O7, Bu3N / 1) PO(OMe)3, 4 deg C, 3 h; 2) DMF, 0 deg C, 1 min View Scheme

1: 46 percent / KOH, tris<2-(2-methoxyethoxy)ethyl>amine / acetonitrile; tetrahydrofuran / 0.17 h / Ambient temperature 2: 67 percent / Bu4NF / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme