1.1: sulfuric acid / 12 h / Reflux 2.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 3.1: triethylamine / dichloromethane / 3 h / 0 °C 4.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 5.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 5.2: 20 h / 20 °C 6.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 7.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 8.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 9.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 11.1: hydrogenchloride / water / 24 h / Reflux 11.2: pH 4 - 5 View Scheme

1.1: diethylamine / ethyl acetate / Reflux 1.2: Reflux 2.1: sulfuric acid / 12 h / Reflux 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 4.1: triethylamine / dichloromethane / 3 h / 0 °C 5.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 6.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 6.2: 20 h / 20 °C 7.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 8.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 9.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 10.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 12.1: hydrogenchloride / water / 24 h / Reflux 12.2: 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: triethylamine / dichloromethane / 3 h / 0 °C 2.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 3.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 3.2: 20 h / 20 °C 4.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 5.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 6.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 7.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 8.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 9.1: hydrogenchloride / water / 24 h / Reflux 9.2: pH 4 - 5 View Scheme

1.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere 1.2: 2 h / -20 °C 1.3: 0 °C 2.1: acetone / water / 80 °C 3.1: ammonia / water / 5 h / 80 °C 3.2: 0 °C / pH 1 4.1: potassium hydroxide / water / 30 h / 0 °C 4.2: 1.17 h / 0 - 80 °C 4.3: 0.5 h / 80 - 90 °C View Scheme

1.1: thionyl chloride / 3.17 h / 0 - 80 °C 2.1: pyridine / dichloromethane / 0.25 h / 0 - 5 °C 2.2: 0.25 h / 0 - 5 °C 2.3: 4 h / 0 - 20 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / nitromethane / 4 h / -25 - -20 °C 4.1: potassium hydroxide; water 4.2: Raney nickel / 20 °C / 2585.81 Torr 4.3: 0 - 3 °C / pH 7 View Scheme

1.1: pyridine / dichloromethane / 0.25 h / 0 - 5 °C 1.2: 0.25 h / 0 - 5 °C 1.3: 4 h / 0 - 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / nitromethane / 4 h / -25 - -20 °C 3.1: potassium hydroxide; water 3.2: Raney nickel / 20 °C / 2585.81 Torr 3.3: 0 - 3 °C / pH 7 View Scheme

1.1: ammonia / water / 5 h / 80 °C 1.2: 0 °C / pH 1 2.1: potassium hydroxide / water / 30 h / 0 °C 2.2: 1.17 h / 0 - 80 °C 2.3: 0.5 h / 80 - 90 °C View Scheme

(S)-α-hydroxybenzeneacetic acid in tetrahydrofuran; water; isopropyl alcohol T=20 - 70°C; 4 h; Resolution of racemate;

1: With (S)-α-hydroxybenzeneacetic acid in water; isopropyl alcohol Resolution of racemate; 2: With hydrogenchloride in water Purification / work up;