N,N,N',N'-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a;2',1'-c][1,4] diazepine-2,12-diamine in N,N-dimethyl-formamide T=20°C; 2 h; Inert atmosphere;

1: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 2: 7.8 g / NaIO4 / CH2Cl2 / 1 h 3: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 4: 0.0876 g / N-chlorosuccinimide; PPh3 / dimethylformamide / 0.67 h / 50 °C 5: 36 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 110 °C View Scheme

1: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 2: 7.8 g / NaIO4 / CH2Cl2 / 1 h 3: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 4: 1.84 g / pyridine / CH2Cl2 / 12 h / 0 - 20 °C 5: 85 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 22 h / 110 °C View Scheme

1: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 2: 7.8 g / NaIO4 / CH2Cl2 / 1 h 3: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 4: 1.84 g / pyridine / CH2Cl2 / 12 h / 0 - 20 °C 5: 97 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 17 h / 110 °C View Scheme

1: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 2: 7.8 g / NaIO4 / CH2Cl2 / 1 h 3: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 4: 1.84 g / pyridine / CH2Cl2 / 12 h / 0 - 20 °C 5: 71 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 46 h / 110 °C View Scheme

1: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 2: 7.8 g / NaIO4 / CH2Cl2 / 1 h 3: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 4: 1.84 g / pyridine / CH2Cl2 / 12 h / 0 - 20 °C 5: 85 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 16 h / 110 °C 6: 83 percent / PIFA; BF3*Et2O / CH2Cl2 / 1.5 h / -25 °C View Scheme