palladium on activated charcoal; hydrogen in methanol T=20°C; P=11251.1 Torr; 3 h;

1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 3.5 h / 100 °C 2: trichlorophosphate / 4 h / 25 - 35 °C 3: bromine / dichloromethane / 2.5 h / 0 °C 4: dichloromethane; toluene / 16 h / |Reflux 5: sodium hydroxide / methanol; water / 3 h / 40 °C 6: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 7: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 8: 10 h / 95 °C 9: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 10: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 3.5 h / 100 °C 2: trichlorophosphate / 4 h / 25 - 35 °C 3: bromine / dichloromethane / 2.5 h / 0 °C 4: dichloromethane; toluene / 16 h / |Reflux 5: sodium hydroxide / methanol; water / 3 h / 40 °C 6: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 7: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 8: 10 h / 95 °C 9: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 10: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: trichlorophosphate / 4 h / 25 - 35 °C 2: bromine / dichloromethane / 2.5 h / 0 °C 3: dichloromethane; toluene / 16 h / |Reflux 4: sodium hydroxide / methanol; water / 3 h / 40 °C 5: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 6: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 7: 10 h / 95 °C 8: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 9: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: bromine / dichloromethane / 2.5 h / 0 °C 2: dichloromethane; toluene / 16 h / |Reflux 3: sodium hydroxide / methanol; water / 3 h / 40 °C 4: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 5: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 6: 10 h / 95 °C 7: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 8: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: dichloromethane; toluene / 16 h / |Reflux 2: sodium hydroxide / methanol; water / 3 h / 40 °C 3: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 4: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 5: 10 h / 95 °C 6: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 7: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: sodium hydroxide / methanol; water / 3 h / 40 °C 2: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 4: 10 h / 95 °C 5: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 6: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 3: 10 h / 95 °C 4: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 5: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 2: 10 h / 95 °C 3: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 4: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1: toluene / 18 h / |Reflux 2: sodium hydrogencarbonate / 1,4-dioxane / 2 h / 20 °C 3: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 12 h / 20 - 25 °C 4: hydrogen; palladium 10 on activated carbon; hydrogenchloride / methanol; water / 3 h / 20 °C / 11251.1 Torr View Scheme