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Boc Protection

(Boc₂O + Base)

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Mechanism:

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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. The base (usually TEA or DIEA) picks up the proton from the protonated amine.
3. tert-Butyl carbonate breaks down into CO2 (gas) and tert-butoxide.

Key Points:

1. The CO2 gas that forms during the reaction should be allowed to escape. Don't run boc protections in closed systems.
2. Base isn't needed for a boc protection reaction to progress (see Boc Protection Boc2O).
3. tert-Butoxide is actually a stronger base than TEA (or DIEA) therefore in the end the proton should end up on tert-butoxide forming tert-butanol.