1: 5 h / 150 °C 2: POCl3 / benzene / Heating 3: pyridine; tetrahydrofuran / 8 h / 0 °C 4: H2 / Ru(OCOCF3)2<(S)-tolbinap> / methanol / 100 h / 30 °C / 76000.1 Torr View Scheme

1: 66 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 2: 81 percent / hydrazine, AcOH / aq. ethanol / 12 h / 50 °C 3: 15 h / 40 °C View Scheme

1: 81 percent / hydrazine, AcOH / aq. ethanol / 12 h / 50 °C 2: 15 h / 40 °C View Scheme

1: trifluoroacetic acid; 5 palladium on charcoal; hydrogen / 48 h / 50 °C / 2585.81 Torr 2: acetone / 1 h / |Reflux 3: sodium tetrahydroborate / methanol; water / 2 h / 0 °C / |Reflux 4: methyl chloroformate / dichloromethane / 2 h / 0 - 20 °C 5: copper(I) oxide / toluene / 16 h / |Reflux 6: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C / |Inert atmosphere 7: hydrazine; acetic acid / ethanol / 12 h / 50 °C / |Inert atmosphere 8: 15 h / 40 °C View Scheme

1: acetone / 1 h / |Reflux 2: sodium tetrahydroborate / methanol; water / 2 h / 0 °C / |Reflux 3: methyl chloroformate / dichloromethane / 2 h / 0 - 20 °C 4: copper(I) oxide / toluene / 16 h / |Reflux 5: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C / |Inert atmosphere 6: hydrazine; acetic acid / ethanol / 12 h / 50 °C / |Inert atmosphere 7: 15 h / 40 °C View Scheme