palladium 10 on activated carbon; hydrogen in methanol T=20°C; 4 h;

hydrogen; palladium on activated charcoal in hydrogenchloride

1: B2H6 / tetrahydrofuran; aq. HCl 2: H2 / Pd-C / aq. HCl View Scheme

1.1: thionyl chloride / 20 - 65 °C 1.2: 0.5 h / 0 °C 2.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 3 h / 0 - 20 °C 3.1: dimethyl sulfoxide / 90 °C 4.1: methanol; potassium carbonate / 1 h / 0 - 20 °C 5.1: 1H-imidazole / dichloromethane / 1.5 h / 20 °C 6.1: lithium borohydride / tetrahydrofuran / 4 h / 0 - 20 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 - 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 9.1: sodium hydride / tetrahydrofuran / 24 h / 0 - 20 °C 10.1: palladium 10 on activated carbon; hydrogen / methanol / 50 °C View Scheme

1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 3 h / 0 - 20 °C 2: dimethyl sulfoxide / 90 °C 3: methanol; potassium carbonate / 1 h / 0 - 20 °C 4: 1H-imidazole / dichloromethane / 1.5 h / 20 °C 5: lithium borohydride / tetrahydrofuran / 4 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 - 20 °C 7: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 8: sodium hydride / tetrahydrofuran / 24 h / 0 - 20 °C 9: palladium 10 on activated carbon; hydrogen / methanol / 50 °C View Scheme

1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 16 h / 0 - 20 °C 2: sodium methylate / methanol / 4 h / |Reflux 3: palladium 10 on activated carbon; hydrogen / methanol / 4 h / 20 °C View Scheme

1: sodium methylate / methanol / 4 h / |Reflux 2: palladium 10 on activated carbon; hydrogen / methanol / 4 h / 20 °C View Scheme

1: thionyl chloride / 2.5 h / 0 - 20 °C 2: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 15 h / 0 - 20 °C 3: sodium tetrahydroborate / ethanol; tetrahydrofuran / 16 h / 0 - 20 °C 4: sodium methylate / methanol / 4 h / |Reflux 5: palladium 10 on activated carbon; hydrogen / methanol / 4 h / 20 °C View Scheme

1: dimethyl sulfoxide / 90 °C 2: methanol; potassium carbonate / 1 h / 0 - 20 °C 3: 1H-imidazole / dichloromethane / 1.5 h / 20 °C 4: lithium borohydride / tetrahydrofuran / 4 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 - 20 °C 6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 7: sodium hydride / tetrahydrofuran / 24 h / 0 - 20 °C 8: palladium 10 on activated carbon; hydrogen / methanol / 50 °C View Scheme

1: methanol; potassium carbonate / 1 h / 0 - 20 °C 2: 1H-imidazole / dichloromethane / 1.5 h / 20 °C 3: lithium borohydride / tetrahydrofuran / 4 h / 0 - 20 °C 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 - 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 6: sodium hydride / tetrahydrofuran / 24 h / 0 - 20 °C 7: palladium 10 on activated carbon; hydrogen / methanol / 50 °C View Scheme