1: 93 percent / pyridine / 20 °C 2: 96 percent / NaN3 / dimethylformamide / 18.5 h / 55 °C 3: 91 percent / H2 / Pd/C / ethanol; H2O / 28 h / 3878.61 Torr View Scheme

1: 82 percent / CBr4; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 20 h / 20 °C 2: 99 percent / NaN3 / dimethylformamide / 55 °C 3: 95 percent / H2 / Pd/C / ethanol; H2O / 28 h / 3878.61 Torr View Scheme

1: 48 percent / morpholinosulfur trifluoride / CH2Cl2 / 20 °C 2: H2 / Pd/C / methanol View Scheme

1.1: 93 percent / PPh3; DIAD / tetrahydrofuran / 3 h 2.1: aq. KHCO3 / dioxane / 14 h 2.2: 1.98 g / diethylaminosulfur trifluoride / CH2Cl2 / 20.75 h / -78 - 20 °C 3.1: H2 / Pd/C / methanol / 19 h View Scheme

1: pyridine 2: H2, / Pd-C View Scheme

1: 84 percent / chromium trioxide; pyridine / CH2Cl2 / 4 h / 20 °C 2: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 3: 2.97 g / aqueous NH4Cl; tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4: 78 percent / thionyl chloride; pyridine / 0.33 h / Heating 5: 90 percent / hydrogen / 10percent Pd/C / ethanol / 20 °C View Scheme

1: 84 percent / chromium trioxide; pyridine / CH2Cl2 / 4 h / 20 °C 2: 48 percent / HMPT; zinc dust / tetrahydrofuran / 3.5 h / Heating 3: 64.3 percent / hydrogen / 10percent Pd/C / ethanol / 20 °C View Scheme