1,4-diaza-bicyclo[2.2.2]octane; hydrogen; palladium on activated charcoal; ethylenediamine in methanol T=20°C; Hydrogenolysis; P=760 Torr; 18 h;

1: CF3COOH / 96 h / Ambient temperature 2: Na2CO3 / dioxane; H2O / 0 °C 3: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 2 h 4: trifluoroacetic acid / 1.5 h / Ambient temperature 5: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature View Scheme

4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane T=0 - 20°C; Inert atmosphere;

zinc trifluoromethanesulfonate in chloroform T=78°C; 18 h;

1: 1.) TFA 2: 44 percent / Zn(OTf)2 / CHCl3 / 18 h / 78 °C View Scheme

1: 1.) TFA 2: 44 percent / Zn(OTf)2 / CHCl3 / 18 h / 78 °C View Scheme

caesium carbonate in N,N-dimethyl-formamide

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