1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere 2.1: triethylamine; hydrogen / palladium on carbon / ethyl acetate / 2 h / 25 °C / 1471.14 Torr 3.1: diisobutylaluminium hydride / toluene / 1 h / -65 - -60 °C / Inert atmosphere 3.2: 1 h / 25 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 4.2: 1.5 h / 25 °C / Inert atmosphere 4.3: pH 5 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere 6.1: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme

sodium hydroxide; hydrogen; palladium on activated carbon in ethyl acetate Product distribution / selectivity;