1: HBr, H2O / diethyl ether / 0.5 h / 0 °C 2: NaHCO3, Na2CO3 / H2O / 2.5 h / Ambient temperature 3: 80 percent / pyridine / 20 h / 0 °C 4: pyridine / CH2Cl2 / 0.33 h / -15 °C 5: 1) Bu4NOAc, 2) DMAP, Py / 1) CH3CN, 40 deg C, 50 min, 2) 3 h, r.t. 6: 93 percent / NaBH4 / ethanol 7: 93 percent / K2CO3 / methanol / 1 h / 0 °C 8: 1) methyl triflate, 2) N-methylimidazole / 1) THF, 0 deg C, 40 min, 2) THF 9: 89 percent / H2, NaOAc / 10percent Pd/C / methanol 10: 95 percent / CF3COOH / H2O; dioxane View Scheme