1: With water; potassium hydroxide Reflux; 2: With hydrogenchloride in water pH=5 - 6;

1.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 2.1: triethylamine / dichloromethane / 3 h / 0 °C 3.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 4.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 4.2: 20 h / 20 °C 5.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 7.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 8.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 9.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

1.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 2.1: triethylamine / dichloromethane / 3 h / 0 °C 3.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 4.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 4.2: 20 h / 20 °C 5.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 7.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 8.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 9.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 10.1: hydrogenchloride / water / 24 h / Reflux 10.2: pH 4 - 5 View Scheme

1.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 2.1: triethylamine / dichloromethane / 3 h / 0 °C 3.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 4.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 4.2: 20 h / 20 °C 5.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 7.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 8.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 9.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 10.1: hydrogenchloride / water / 24 h / Reflux 10.2: pH 4 - 5 View Scheme

1.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 2.1: triethylamine / dichloromethane / 3 h / 0 °C 3.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 4.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 4.2: 20 h / 20 °C 5.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 7.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 8.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 9.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 10.1: hydrogenchloride / water / 24 h / Reflux 10.2: pH 4 - 5 View Scheme