1.1: n-dipropylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 4.2: pH 2 5.1: acetone / water / 80 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 7.1: potassium hydroxide / water / 30 h / 0 °C 7.2: 1.17 h / 0 - 80 °C 7.3: 0.5 h / 80 - 90 °C View Scheme

1.1: hydrogen bromide / water / 72 h / 100 °C 2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 3.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 3.2: pH 2 4.1: acetone / water / 80 °C 5.1: ammonia / water / 5 h / 80 °C 5.2: 0 °C / pH 1 6.1: potassium hydroxide / water / 30 h / 0 °C 6.2: 1.17 h / 0 - 80 °C 6.3: 0.5 h / 80 - 90 °C View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal 1.) EtOH, 2 atm, 2.) reflux, 24 h; Yield given. Multistep reaction;

1.1: sodium hydroxide 2.1: diethylamine / ethyl acetate / Reflux 2.2: Reflux 3.1: sulfuric acid / 12 h / Reflux 4.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 5.1: triethylamine / dichloromethane / 3 h / 0 °C 6.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 7.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 7.2: 20 h / 20 °C 8.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 9.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 10.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 11.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 13.1: hydrogenchloride / water / 24 h / Reflux 13.2: pH 4 - 5 View Scheme

1.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 2.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 3.1: hydrogenchloride / water / 24 h / Reflux 3.2: pH 4 - 5 View Scheme

1.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 2.1: hydrogenchloride / water / 24 h / Reflux 2.2: pH 4 - 5 View Scheme

1.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 2.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 2.2: 20 h / 20 °C 3.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 5.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 6.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 7.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 8.1: hydrogenchloride / water / 24 h / Reflux 8.2: pH 4 - 5 View Scheme

1.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 1.2: 20 h / 20 °C 2.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 4.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 5.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 6.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 7.1: hydrogenchloride / water / 24 h / Reflux 7.2: pH 4 - 5 View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 2.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 3.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 4.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 5.1: hydrogenchloride / water / 24 h / Reflux 5.2: pH 4 - 5 View Scheme

1.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 2.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 3.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 4.1: hydrogenchloride / water / 24 h / Reflux 4.2: pH 4 - 5 View Scheme