1: 2.) sodium borohydride 2: H2 / palladium black / acetic acid View Scheme

1: 81 percent / aq. trifluoroacetic acid, sodium borohydride 2: 92 percent / H2 / palladium black / acetic acid View Scheme

1: copper(II) sulfate; acetic acid; zinc / tetrahydrofuran; water / 0.33 h / Inert atmosphere 2: sodium methylate / methanol / 16 h / 20 °C / Inert atmosphere 3: hydrogenchloride; palladium 10 on activated carbon; hydrogen / water / 24 h / 20 °C / Inert atmosphere 4: Dowex (50W-X8, H+) / water / Inert atmosphere View Scheme

1: sodium methylate / methanol / 16 h / 20 °C / Inert atmosphere 2: hydrogenchloride; palladium 10 on activated carbon; hydrogen / water / 24 h / 20 °C / Inert atmosphere 3: Dowex (50W-X8, H+) / water / Inert atmosphere View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h 2.1: sodium methylate / methanol / 0.5 h / 20 °C 2.2: resin Amberlite IR-120, H+ 3.1: palladium on carbon; hydrogen; ammonium formate / methanol; water / 48 h / 20 °C / 760.05 Torr View Scheme

1.1: potassium carbonate; copper(II) sulfate / methanol 2.1: pyridine / dichloromethane / 6 h / 20 °C 3.1: sodium iodide / N,N-dimethyl-formamide / 4 h / 100 °C 4.1: dichloromethane; pyridine / 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / |Reflux 6.1: tributylphosphine / tetrahydrofuran; water / 0 °C 6.2: 5 h 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h 8.1: sodium methylate / methanol / 0.5 h / 20 °C 8.2: resin Amberlite IR-120, H+ 9.1: palladium on carbon; hydrogen; ammonium formate / methanol; water / 48 h / 20 °C / 760.05 Torr View Scheme

1.1: pyridine / dichloromethane / 6 h / 20 °C 2.1: sodium iodide / N,N-dimethyl-formamide / 4 h / 100 °C 3.1: dichloromethane; pyridine / 20 °C 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / |Reflux 5.1: tributylphosphine / tetrahydrofuran; water / 0 °C 5.2: 5 h 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h 7.1: sodium methylate / methanol / 0.5 h / 20 °C 7.2: resin Amberlite IR-120, H+ 8.1: palladium on carbon; hydrogen; ammonium formate / methanol; water / 48 h / 20 °C / 760.05 Torr View Scheme

1.1: sodium methylate / methanol / 0.5 h / 20 °C 1.2: resin Amberlite IR-120, H+ 2.1: palladium on carbon; hydrogen; ammonium formate / methanol; water / 48 h / 20 °C / 760.05 Torr View Scheme