Multi-step reaction with 9 steps
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
With
pyridine; lithium hydroxide; sodium hydroxide; n-butyllithium; trifluoro-[1,3,5]triazine; lithium peroxide; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; hydrogen; dihydrogen peroxide; triethylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jm00068a008