lithium hydroxide 1.) THF, H2O; 2.) Et2O; Yield given. Multistep reaction;

暂无反应条件数据

1.1: 96 percent / HBr / 0.5 h / 45 °C 2.1: NaN3 / dimethylformamide / 12 h / 50 °C 3.1: NaOAc / methanol / 12 h 4.1: Et3N; DMAP / ethyl acetate / 4 h / 20 °C 4.2: 92 percent / H2 / Pd/C / ethyl acetate; methanol / 48 h View Scheme

1.1: 90 percent / thionyl chloride; triethylamine / CH2Cl2 / 0.75 h / 0 °C 2.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 °C 3.1: 88 percent / Et3N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr 4.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C 4.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C 5.1: 80 percent / tri-n-butyltin hydride; AIBN / toluene / Heating 6.1: 81 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: p-TsOH / CH2Cl2 / 5 h / Ambient temperature 2: AcBr / CH2Cl2 / 2 h / -15 °C 3: NaN3 / dimethylformamide / 50 °C 4: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature 5: 10percent aq. HCl / 2 h / Heating 6: aq. NaOH / 3 h / Ambient temperature View Scheme

1: With sulfuric acid; acetonitrile T=-10 - 20°C; 2: With hydrogenchloride Heating;

1: p-TsOH*H2O / CH2Cl2 / 2.5 h / Ambient temperature 2: 94 percent / ZnBr2 / CH2Cl2 / -15 deg C, 1 h then 0 deg C, 2 h 3: 78 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C 4: 87 percent / K2CO3 / methanol / 0.33 h / 0 °C 5: 91 percent / H2 / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature 6: 79 percent / pyridinium p-toluenesulfonate / benzene / 90 °C 7: LiOH / methanol; H2O / 1 h / Ambient temperature View Scheme

1: p-TsOH*H2O / CH2Cl2 / 2.5 h / Ambient temperature 2: 94 percent / ZnBr2 / CH2Cl2 / -15 deg C, 1 h then 0 deg C, 2 h 3: 78 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C 4: 87 percent / K2CO3 / methanol / 0.33 h / 0 °C 5: 91 percent / H2 / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature View Scheme

1.1: 90 percent / thionyl chloride; triethylamine / CH2Cl2 / 0.75 h / 0 °C 2.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 °C 3.1: 88 percent / Et3N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr 4.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C 4.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C 5.1: 80 percent / tri-n-butyltin hydride; AIBN / toluene / Heating View Scheme

hydrogenchloride; 5 palladium on charcoal; hydrogen in methanol T=25°C; P=1275.13 - 3000.3 Torr; 30 h;