1.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 2.1: DCC / tetrahydrofuran / 6 h / Heating 3.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 3.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 4.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C 5.1: NaBH4 / H2O; acetonitrile / 0.25 h View Scheme

1.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 2.1: DCC / tetrahydrofuran / 6 h / Heating 3.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 3.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 4.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme