1: NaBH4 / methanol / 0.5 h / Ambient temperature 2: Et3N / CH2Cl2 3: 77 percent / NaN3 / dimethylformamide / 24 h / 80 °C 4: 98 percent / 5percent HCl / methanol / 0.25 h / Ambient temperature 5: 1.) SOCl2, Et3N, 2.) NaIO4, RuCl3 / 1.) CH2Cl2, room temperature, 15 min, 2.) CCl4, CH3CN, H2O, room temperature, 1 h 6: 82 percent / H2 / Pd/C / tetrahydrofuran; H2O / 2 h / 1551.4 Torr 7: conc. H2SO4, H2O / tetrahydrofuran / 1 h / Heating 8: K2CO3 / CH2Cl2 / 18 h / Ambient temperature 9: 85 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -70 - 20 °C View Scheme