hydrogen; palladium on activated charcoal in methanol P=2585.7 Torr; 4 h;

1: 96 percent / trifluoromethanesulfonic acid / CH2Cl2 / 1.) -78 deg C, 15 min, 2.) -20 deg C 45 min 2: 97 percent / aq. 1N NaOH / dioxane / 3 h / Ambient temperature 3: 99 percent / pyridine, cyanuric fluoride / acetonitrile / 2 h / Ambient temperature 4: 1.) 2.5 N BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1 h 5: 1.) 1 N lithium hexamethyldisilazane / 1.) THF, 30 min, 2.) THF, 0 deg C, 1 h 6: 99 percent / lithium peroxide, 30percent H2O2, lithium hydroxide monohydrate / tetrahydrofuran; H2O / 1 h 7: triethylamine, diphenyl phosphorazidate / toluene / 0.5 h / 80 °C 8: 92 percent / 3 h 9: 100 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr View Scheme

1: 99 percent / pyridine, cyanuric fluoride / acetonitrile / 2 h / Ambient temperature 2: 1.) 2.5 N BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1 h 3: 1.) 1 N lithium hexamethyldisilazane / 1.) THF, 30 min, 2.) THF, 0 deg C, 1 h 4: 99 percent / lithium peroxide, 30percent H2O2, lithium hydroxide monohydrate / tetrahydrofuran; H2O / 1 h 5: triethylamine, diphenyl phosphorazidate / toluene / 0.5 h / 80 °C 6: 92 percent / 3 h 7: 100 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr View Scheme

1: 97 percent / aq. 1N NaOH / dioxane / 3 h / Ambient temperature 2: 99 percent / pyridine, cyanuric fluoride / acetonitrile / 2 h / Ambient temperature 3: 1.) 2.5 N BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1 h 4: 1.) 1 N lithium hexamethyldisilazane / 1.) THF, 30 min, 2.) THF, 0 deg C, 1 h 5: 99 percent / lithium peroxide, 30percent H2O2, lithium hydroxide monohydrate / tetrahydrofuran; H2O / 1 h 6: triethylamine, diphenyl phosphorazidate / toluene / 0.5 h / 80 °C 7: 92 percent / 3 h 8: 100 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr View Scheme

1: 1.) 2.5 N BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1 h 2: 1.) 1 N lithium hexamethyldisilazane / 1.) THF, 30 min, 2.) THF, 0 deg C, 1 h 3: 99 percent / lithium peroxide, 30percent H2O2, lithium hydroxide monohydrate / tetrahydrofuran; H2O / 1 h 4: triethylamine, diphenyl phosphorazidate / toluene / 0.5 h / 80 °C 5: 92 percent / 3 h 6: 100 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr View Scheme