1: 57 percent / 75 °C / 0.08 - 0.1 Torr 2: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 4: 80 percent / 0.67 h / 105 - 110 °C 5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 2: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 3: 80 percent / 0.67 h / 105 - 110 °C 4: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 5: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 6: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 7: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 8: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 88 percent / methanol / 2 h / Ambient temperature 2: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 2: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 3: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 4: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 5: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 2: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 2: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 4: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 4: 80 percent / 0.67 h / 105 - 110 °C 5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 4: 80 percent / 0.67 h / 105 - 110 °C 5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

1: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme