1,4-diaza-bicyclo[2.2.2]octane in dichloromethane

1: NaBH4, NaOH / methanol / 1 h / 25 °C 2: 1.) NaH / 1) ether, 1 h; 2) ether, 4 h View Scheme

sodium tetrahydroborate in dimethyl sulfoxide 5 h; Ambient temperature;

sodium hydroxide in methanol; dichloromethane T=20°C; 16 h;

hydrogen; palladium on activated charcoal in ethyl acetate

potassium bromide in diethylene glycol

1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.92 h / -78 °C / Inert atmosphere 2: lithium aluminium tetrahydride / diethyl ether / -40 °C 3: potassium phosphate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-cyclo-hexyl-phosphine / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere View Scheme