1: 78 percent / Ph3P, DEAD / tetrahydrofuran / 0.5 h / Heating 2: 33 percent / LiAlH4 / tetrahydrofuran / 48 h / Heating View Scheme

1: water; zinc–copper couple; hydrogenchloride / methanol / 18 h / 25 °C 2: sodium carbonate; magnesium sulfate / ethanol; water / 23 h / 25 °C 3: toluene / 5 h / |Reflux 4: hydrogen; palladium 10 on activated carbon / methanol / 18 h / 30 °C / 2250.23 Torr View Scheme

1: 88 percent / aq. N-methylmorpholine N-oxide; OsO4 / acetone / 2.5 h / 20 °C 2: 84 percent / p-TsOH / acetone / 20 °C 3: 92 percent / MeNH2 / ethanol / 2 h / Heating View Scheme

1: zinc / ethanol / 1 h / 70 °C 2: sodium carbonate / ethanol / 1 h / 50 °C 3: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 4: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C View Scheme

1: sodium iodide / butanone / 22 h / 80 °C 2: zinc; water; hydrogenchloride / ethanol / 19 h / 10 - 24 °C 3: sodium carbonate; magnesium sulfate / ethanol; water / 23 h / 25 °C 4: toluene / 5 h / |Reflux 5: hydrogen; palladium 10 on activated carbon / methanol / 18 h / 30 °C / 2250.23 Torr View Scheme

1.1: 33 g / tetrakis(triphenylphosphine)palladium / tetrahydrofuran; dimethylsulfoxide / 3 h / Heating 2.1: pyridine; DMAP / CH2Cl2 / 20 h / 20 °C 3.1: Pseudomonas cepacia lipase; aq. NaOH; phosphate buffer / acetone / 18 h / pH 7 3.2: N-methylmorpholine N-oxide; OsO4 / acetone 4.1: p-toluenesulfonic acid / acetone / 15 h 5.1: NH3 / methanol / 6 h View Scheme

1: perchloric acid / acetone / 24 h / Molecular sieve 2: pyridine / 24 h / 20 °C 3: sodium iodide / butanone / 24 h / 120 °C 4: zinc / ethanol / 1 h / 70 °C 5: sodium carbonate / ethanol / 1 h / 50 °C 6: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 7: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 2.2: 3 h / 20 °C 3.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 4.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C 5.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 6.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 8.1: hydrogenchloride; water / methanol / 1 h View Scheme

1.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 2.2: 3 h / 20 °C 3.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 4.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C View Scheme

N-ethyl-N,N-diisopropylamine