1: 62 percent / pyridine / Ambient temperature 2: imidazole / dimethylformamide / 80 °C 3: 1N NaOH / methanol / Ambient temperature 4: 91 percent / DMSO/DCC/TFA / pyridine; benzene / Ambient temperature 5: 87 percent / K2CO3 / methanol / Ambient temperature 6: 99 percent / H2NOH.HCl, NaHCO3 / ethanol; H2O / 60 °C 7: LiAlH4 / tetrahydrofuran / Ambient temperature 8: tetrahydrofuran; H2O / 0 °C 9: 41 percent / TsOH / methanol; H2O / 15 °C 10: methoxyethanol / Heating 11: 1.) borane-THF complex 2.) 6N HCl / 1.) THF, reflux, 2.) THF, reflux View Scheme

sodium periodate in tetrahydrofuran; water 1 h;

1: 85 percent / sodium periodate / tetrahydrofuran; H2O / 1 h 2: 19 percent / CH2Cl2 / 40 h / -18 °C View Scheme