lithium aluminium tetrahydride in diethyl ether T=20°C; 18 h;

1: 60 percent / NaOEt; NaI / ethanol / 48 h / Heating 2: 94 percent / LiAlH4 / diethyl ether / 18 h / 20 °C View Scheme

lithium aluminium tetrahydride; sodium hydride 1.) EtOH, reflux, 48 h, 2.) Et2O; Yield given. Multistep reaction;

1.1: 83 percent / Dowex 50WX8-H(1+) resin / ethanol / 2 h / Heating 2.1: 99 percent / NEt3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 47 percent / HCl / H2O; dioxane / 18 h / 20 °C 4.1: 95 percent / NEt3; DMAP; 3 Angstroem molecular sieves / acetonitrile / 1 h / 20 °C 5.1: bis(trimethylsilyl)acetamide / 1-methyl-pyrrolidin-2-one / 80 °C 5.2: 70 percent / TMSOTf / 1-methyl-pyrrolidin-2-one / 24 h / 0 °C 6.1: 87 percent / aq. NaOH / 3 h / 20 °C 7.1: 10 percent / DIBAL-H / tetrahydrofuran / 48 h / 20 °C View Scheme

T=20°C; lipase P;

1.1: 83 percent / Dowex 50WX8-H(1+) resin / ethanol / 2 h / Heating 2.1: 99 percent / NEt3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 47 percent / HCl / H2O; dioxane / 18 h / 20 °C 4.1: 95 percent / NEt3; DMAP; 3 Angstroem molecular sieves / acetonitrile / 1 h / 20 °C 5.1: bis(trimethylsilyl)acetamide / dimethylformamide / 1.5 h / 20 °C 5.2: 81 percent / TMSOTf / dimethylformamide / 3 h / 0 - 5 °C 6.1: 42 percent / aq. NaOH / dioxane / 4 h / 20 °C 7.1: DIBAL-H / tetrahydrofuran / 24 h / 20 °C 8.1: NEt3; DMAP / CH2Cl2 / 2 h / Heating View Scheme

1.1: 83 percent / Dowex 50WX8-H(1+) resin / ethanol / 2 h / Heating 2.1: 99 percent / NEt3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 47 percent / HCl / H2O; dioxane / 18 h / 20 °C 4.1: 95 percent / NEt3; DMAP; 3 Angstroem molecular sieves / acetonitrile / 1 h / 20 °C 5.1: bis(trimethylsilyl)acetamide / dimethylformamide / 1.5 h / 20 °C 5.2: 81 percent / TMSOTf / dimethylformamide / 3 h / 0 - 5 °C 6.1: 42 percent / aq. NaOH / dioxane / 4 h / 20 °C 7.1: DIBAL-H / tetrahydrofuran / 24 h / 20 °C 8.1: NEt3; DMAP / CH2Cl2 / 2 h / Heating 9.1: 81 percent / hydrogen; NEt3 / Pd/C / ethyl acetate / 4 h / 50 °C / 760 Torr View Scheme

1.1: 83 percent / Dowex 50WX8-H(1+) resin / ethanol / 2 h / Heating 2.1: 99 percent / NEt3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 47 percent / HCl / H2O; dioxane / 18 h / 20 °C 4.1: 95 percent / NEt3; DMAP; 3 Angstroem molecular sieves / acetonitrile / 1 h / 20 °C 5.1: bis(trimethylsilyl)acetamide / dimethylformamide / 1.5 h / 20 °C 5.2: 81 percent / TMSOTf / dimethylformamide / 3 h / 0 - 5 °C 6.1: 42 percent / aq. NaOH / dioxane / 4 h / 20 °C 7.1: DIBAL-H / tetrahydrofuran / 24 h / 20 °C View Scheme