water; sodium hydroxide in methanol; dichloromethane Reflux;

1: 1.) LDA / 1.) hexane, THF, 2.) hexane, THF, 20 deg C, 15 min 2: sodium borohydride / tetrahydrofuran; H2O / 2 h / 20 °C 3: acetonitrile / 3 h / Heating 4: sodium borohydride / methanol / 1 h / 25 °C 5: H2, aq. HCl / Pd/C / aq. ethanol / 16 h / 65 °C View Scheme

lithium diisopropyl amide 1.) hexane, THF, 2.) hexane, THF, 20 deg C, 15 min; Yield given. Multistep reaction;