1.1: 4-methylmorpholine N-oxide; OsO4 / tetrahydrofuran; H2O / 20 °C 1.2: 48 percent / NaIO4 / methanol; tetrahydrofuran; H2O / 2 h / 20 °C 2.1: 92 percent / NaBH4 / ethanol / 2 h 3.1: 61 percent / H2 / Pd/C / methanol / 18 h / 20 °C 4.1: 45 percent / DMAP; pyridine / 18 h / 0 - 20 °C 5.1: 100 percent / H2 / PtO2 / methanol / 18 h View Scheme

1.1: 4-methylmorpholine N-oxide; OsO4 / tetrahydrofuran; H2O / 20 °C 1.2: 48 percent / NaIO4 / methanol; tetrahydrofuran; H2O / 2 h / 20 °C 2.1: 92 percent / NaBH4 / ethanol / 2 h 3.1: 61 percent / H2 / Pd/C / methanol / 18 h / 20 °C View Scheme