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Boc Protection

(Boc2O)







Mechanism:



Boc protection mechanism


Steps:

  1. The amine attacks a carbonyl site on di-tert-butyl dicarbonate (Boc2O) resulting in tert-butyl carbonate leaving as a leaving group.
  2. Tert-butyl carbonate picks up the proton from the protonated amine.
  3. Tert-butyl bicarbonate breaks down into CO2 (gas) and tert-butanol.

Key Points:

  1. The CO2 gas that forms during the rxn should be allowed to escape. Don't run boc protections in closed systems.
  2. No base is needed for the rxn. The second proton that was originally on the amine starting material ends up on tert-butanol. Some boc protections, however, are done with base (see Boc Protection home page).



Related Books: