1.1: sulfuric acid; urea; sodium nitrite / water / 2 h / 0 °C 1.2: 5 h / 25 °C 2.1: borane-THF 3.1: pyridinium chlorochromate / dichloromethane / 25 °C View Scheme

hydrogenchloride; 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane; acetic acid 1.) CHCl3, reflux, 15 h, 2.) reflux, 30 min; Yield given. Multistep reaction;

1.1: / tetrahydrofuran / 20 h / -60 - 20 °C / |Inert atmosphere 2.1: hydrogenchloride; zinc / 1 h / 0 °C / |Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C / |Inert atmosphere 4.1: copper(l) chloride; potassium tert-butylate; 1,10-phenanthroline / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere 4.2: 18 h / 50 °C / |Inert atmosphere 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C / |Inert atmosphere 5.2: 18 h / 20 °C View Scheme

1.1: / tetrahydrofuran / 20 h / -60 - 20 °C / |Inert atmosphere 2.1: hydrogenchloride; zinc / 1 h / 0 °C / |Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C / |Inert atmosphere 4.1: copper(l) chloride; potassium tert-butylate; 1,10-phenanthroline / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere 4.2: 18 h / 50 °C / |Inert atmosphere View Scheme