chlorine in dichloromethane T=0 - 20°C; 4 h;

1: 11.5 g / KOH / ethanol / Heating 2: PCl5 / toluene / 1 h / Heating View Scheme

1: H2 / Pd-C / ethanol 2: 11.5 g / KOH / ethanol / Heating 3: PCl5 / toluene / 1 h / Heating View Scheme

1.1: nitric acid; acetic acid 2.1: hydrogen / platinum on carbon / methanol / 1 h / 2844.39 Torr 3.1: pyridine / 0.5 h / Reflux 3.2: 20 °C / Cooling with ice 4.1: chlorine / chloroform / 20 °C / Cooling with ice View Scheme

1: With lithium hexamethyldisilazane in tetrahydrofuran T=-20°C; 2: With N-chloro-succinimide in tetrahydrofuran T=-20 - 20°C;

in dichloromethane; N,N-dimethyl-formamide T=20 - 25°C; 1.75 h;

ammonium hydroxide

1.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; water; acetonitrile / 10.08 h / 20 - 40 °C 3.1: tetrahydrofuran / 5 - 60 °C 4.1: sodium acetate; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 15 - 20 °C 5.1: tetrahydrofuran / 4.92 h / 20 °C / Resolution of racemate 5.2: 22.25 h / 20 °C / Resolution of racemate View Scheme

1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; water; acetonitrile / 10.08 h / 20 - 40 °C 3: tetrahydrofuran / 5 - 60 °C 4: sodium acetate; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 15 - 20 °C View Scheme

triethylamine in N,N-dimethyl-formamide T=75°C; 2 h;