1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature 2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 3: toluene / 24 h / Heating 4: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 5: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 8: 80 percent / 0.67 h / 105 - 110 °C 9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h 14: 95 percent / CH2Cl2 View Scheme

1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature 2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 3: toluene / 24 h / Heating 4: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 5: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 8: 80 percent / 0.67 h / 105 - 110 °C 9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

hydrogenchloride 24 h; Heating;

hydrogenchloride T=110°C; 14 h;