1,4-diaza-bicyclo[2.2.2]octane in acetonitrile 16 h; Heating;

boron tribromide in dichloromethane a) -78 deg C, 1 h, b) without cooling, 20 h;

1: 1) s-BuLi, N,N,N,N-tetramethylethylene diamine / 1) THF, cyclohexane, -78 deg C, 1 h, 2) to room temperature, 12 h 2: 1) LDA / 1) a) THF, 0 deg C, 1.5 h, b) 40-45 deg C, 0.5 h, 2) THF, 40 deg C, 12 h 3: p-toluenesulfonic acid / toluene / 12 h / Heating 4: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 1 h, b) without cooling, 20 h View Scheme

1.1: potassium carbonate / methanol; dichloromethane / 2 h / Inert atmosphere; Reflux 2.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere 3.1: triphenylphosphine / acetonitrile / 1 h / Inert atmosphere; Reflux 3.2: 9 h / 20 °C / Inert atmosphere; Reflux 4.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 5.1: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme

1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 2: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme

1.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / methanol; dichloromethane / 2 h / Inert atmosphere; Reflux 3.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere 4.1: triphenylphosphine / acetonitrile / 1 h / Inert atmosphere; Reflux 4.2: 9 h / 20 °C / Inert atmosphere; Reflux 5.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 6.1: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme

1.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere 2.1: triphenylphosphine / acetonitrile / 1 h / Inert atmosphere; Reflux 2.2: 9 h / 20 °C / Inert atmosphere; Reflux 3.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 4.1: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme

1.1: triphenylphosphine / acetonitrile / 1 h / Inert atmosphere; Reflux 1.2: 9 h / 20 °C / Inert atmosphere; Reflux 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 3.1: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / Inert atmosphere 2.1: tetrahydrofuran / Inert atmosphere 3.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 3.2: 8 h / -78 - 20 °C / Inert atmosphere 4.1: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere 5.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / methanol; dichloromethane / 2 h / Inert atmosphere; Reflux 7.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere 8.1: triphenylphosphine / acetonitrile / 1 h / Inert atmosphere; Reflux 8.2: 9 h / 20 °C / Inert atmosphere; Reflux 9.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 10.1: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme

1.1: tetrahydrofuran / Inert atmosphere 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 2.2: 8 h / -78 - 20 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere 4.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / methanol; dichloromethane / 2 h / Inert atmosphere; Reflux 6.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere 7.1: triphenylphosphine / acetonitrile / 1 h / Inert atmosphere; Reflux 7.2: 9 h / 20 °C / Inert atmosphere; Reflux 8.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C / 6000.6 Torr 9.1: chromium(VI) oxide; acetic acid / dichloromethane / 42 h / 20 °C / Inert atmosphere View Scheme