lithium aluminium tetrahydride in tetrahydrofuran T=0°C;

trichlorophosphate T=70°C; 1 h;

1: 71 percent / DBU / tetrahydrofuran / 4.5 h / 0 - 20 °C 2: 72 percent / LiAlH4 / tetrahydrofuran / 0 °C View Scheme

1: n-BuNH2 / toluene / Heating 2: 71 percent / DBU / tetrahydrofuran / 4.5 h / 0 - 20 °C 3: 72 percent / LiAlH4 / tetrahydrofuran / 0 °C View Scheme

1: n-BuNH2 / toluene / Heating 2: 71 percent / DBU / tetrahydrofuran / 4.5 h / 0 - 20 °C 3: 72 percent / LiAlH4 / tetrahydrofuran / 0 °C View Scheme

1: pyridine; bromine / cyclohexane / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 20 °C / Inert atmosphere; Reflux 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; isopropyl alcohol / 0 - 20 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere View Scheme

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 20 °C / Inert atmosphere; Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; isopropyl alcohol / 0 - 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere View Scheme

1: urea; sodium nitrite / N,N-dimethyl-formamide / -10 °C / Inert atmosphere 2: acetic acid / methanol / 2.5 h / 20 °C / Inert atmosphere 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; isopropyl alcohol / 0 - 20 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere View Scheme

1: acetic acid / methanol / 2.5 h / 20 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; isopropyl alcohol / 0 - 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere View Scheme

1: phosphorus tribromide / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere 2: urea; sodium nitrite / N,N-dimethyl-formamide / -10 °C / Inert atmosphere 3: acetic acid / methanol / 2.5 h / 20 °C / Inert atmosphere 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; isopropyl alcohol / 0 - 20 °C / Inert atmosphere 5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere View Scheme