1.1: NaBH4; isobutyric acid / toluene / 3 h / 0 °C 1.2: HBr / ethyl acetate; propionic acid / 0 °C 1.3: aq. NaHCO3 2.1: Na / ethanol / 15 h / 80 °C 3.1: HCl / ethyl acetate; dioxane / 0 - 20 °C 4.1: LiOH*H2O / tetrahydrofuran; ethanol; H2O / 36 h / 0 °C 5.1: HCO2NH4 / Pd/C / methanol / 2 h / Heating 6.1: NaHCO3 / acetone; H2O / 0 - 20 °C View Scheme

1.1: sodium tetrahydroborate; acetic acid / acetonitrile / 2 - 22 °C / Inert atmosphere 1.2: pH ~ 8 2.1: sodium t-butanolate / tert-butyl alcohol; tetrahydrofuran / 5 h / 6 - 22 °C / Inert atmosphere 3.1: lithium borohydride / tetrahydrofuran / 12 h / 15 °C / Reflux; Inert atmosphere 3.2: 0.5 h / 5 - 15 °C 3.3: pH ~ 8.7 4.1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere 5.1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere 6.1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 7.1: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 8.1: hydrogenchloride; water / 4 h / Reflux 9.1: thionyl chloride / dichloromethane View Scheme