1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane; sulfuric acid; acetic acid T=25°C; 18 h;

1: N-bromosuccinmide; sulfuric acid / tetrahydrofuran / |Inert atmosphere 2: triethylamine; magnesium chloride / acetonitrile / |Inert atmosphere View Scheme

N-bromosuccinmide; sulfuric acid in tetrahydrofuran Inert atmosphere;

1: 80 percent / potassium carbonate, N, N-dimethylformamide / 1.5 h / Heating 2: 49 percent / trifluoroacetic acid / 0.25 h / Heating 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating 5: hydrochloric acid / ethanol View Scheme

1: 80 percent / potassium carbonate, N, N-dimethylformamide / 1.5 h / Heating 2: 49 percent / trifluoroacetic acid / 0.25 h / Heating View Scheme

1: 80 percent / potassium carbonate, N, N-dimethylformamide / 1.5 h / Heating 2: 49 percent / trifluoroacetic acid / 0.25 h / Heating 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating View Scheme

1: 80 percent / potassium carbonate, N, N-dimethylformamide / 1.5 h / Heating 2: 49 percent / trifluoroacetic acid / 0.25 h / Heating 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating 5: hydrochloric acid / ethanol 6: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme