Methyl carbamate

Methyl carbamate scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • ClCO2Me Et3N DMAP
    CH2Cl2
    RT
    4 h
    87 %
    intermediate structure
    ClCO2Me, Et3N, DMAP
    CH2Cl2
    RT, 4 h, 87%
    intermediate structure
  • ClCO2Me TMS2NNa
    THF
    -78 °C - RT
    4 h
    96 %
    intermediate structure
    ClCO2Me, TMS2NNa
    THF
    -78 °C to RT, 4 h, 96%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TMSI
    CHCl3
    Reflux
    6 h
    100 %
    intermediate structure
    TMSI
    CHCl3
    Reflux, 6 h, 100%
    intermediate structure
  • HBr
    AcOH
    RT
    22 h
    74 %
    intermediate structure
    HBr
    AcOH
    RT, 22 h, 74%
    intermediate structure