1: 91 percent / pyridine / 13 h / 0 °C 2: 51 percent / NaN3 / dimethylformamide / 0.42 h / 140 - 145 °C 3: 65 percent / H2 / Pd black / ethanol / 14 h / 760 Torr / Ambient temperature 4: 100 percent / K2CO3 / acetone / 1 h / Ambient temperature 5: 80 percent / conc. HCl / methanol / 14 h / Ambient temperature 6: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 2.) -20 deg C 7: 1.) CuI, THF-Me2S / 1.) THF, -78 deg C, 2.) -78 deg C 8: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 9: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 2.) 60 deg C 10: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme