Carbonate

Carbonate scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • Triphosgene Pyr
    CH2Cl2
    -78 - 0 °C
    30 - 70 min
    92-100 %
    intermediate structure
    Triphosgene, Pyr
    CH2Cl2
    0 °C, 30 min, 92%
    intermediate structure
    intermediate structure
    Triphosgene, Pyr
    CH2Cl2
    -78 to 0 °C, 60 min, 94%
    intermediate structure
    intermediate structure
    Triphosgene, Pyr
    CH2Cl2
    -45 °C, 70 min, 100%
    intermediate structure
  • Phosgene Pyr
    PhMe
    -78 - -23 °C
    30 min
    100 %
    intermediate structure
    Phosgene, Pyr
    PhMe
    -78 to -23 °C, 30 min, 100%
    intermediate structure
  • CDI NaH
    DMF
    RT
    20 min
    81 %
    intermediate structure
    CDI, NaH
    DMF
    RT, 20 min, 81%
    intermediate structure
  • CDI
    PhH
    RT
    60 min
    76 %
    intermediate structure
    CDI
    PhH
    RT, 60 min, 76%
    "Also isolated was the desired regioisomer (18 % yield, see next step)."
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • KOH
    MeOH
    RT
    30 min
    89 %
    intermediate structure
    KOH
    MeOH
    RT, 30 min, 89%
    intermediate structure