1.1: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 2.1: borane-THF / ethanol; tetrahydrofuran / 13 h 3.1: triethylamine / dichloromethane / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / |Reflux 5.1: ethanol 6.1: sodium hydroxide / ethyl acetate 6.2: 18 h / |Reflux 7.1: hydrogen; 10 palladium hydroxide on charcoal / acetic acid / 24 h / 20 °C / 3675.37 Torr View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / -10 °C / Inert atmosphere 2.1: potassium hydroxide; water / 4 h / Reflux 2.2: 20 °C 3.1: ethyl acetate / 1.25 h / 0 °C / Reflux 4.1: hydrogenchloride / dichloromethane; water / 0.08 h 5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 6.1: dichloromethane; water / 0 - 10 °C 7.1: borane-THF / tetrahydrofuran / 20 - 50 °C 7.2: 0.25 h / 0 - 5 °C 7.3: 2.5 h / 0 °C / Reflux 8.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 8.2: 2 h / 20 °C 9.1: potassium carbonate / water / 0.08 h 9.2: Inert atmosphere 10.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / -10 °C / Inert atmosphere 2.1: potassium hydroxide; water / 4 h / Reflux 2.2: 20 °C 3.1: ethyl acetate / 1.25 h / 0 °C / Reflux 4.1: hydrogenchloride / dichloromethane; water / 0.08 h 5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 6.1: dichloromethane; water / 0 - 10 °C 7.1: borane-THF / tetrahydrofuran / 20 - 50 °C 7.2: 0.25 h / 0 - 5 °C 7.3: 2.5 h / 0 °C / Reflux 8.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 8.2: 2 h / 20 °C 9.1: potassium carbonate / water / 0.08 h 9.2: Inert atmosphere View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / -10 °C / Inert atmosphere 2.1: potassium hydroxide; water / 4 h / Reflux 2.2: 20 °C View Scheme