Boc removed from an amine
Acid takes the carbamate off, leaving the free amine.
What it needs, and what it gives
- Reaction class
- Deprotection
- Trifluoroacetic acid, or hydrogen chloride in dioxane.
- not stated
- Mechanism
- Acid removal of a Boc group, 3 steps
How it is thought to happen
Acid protonates the carbamate, the tert-butyl group leaves as a cation because it can, and what is left gives off carbon dioxide to free the amine.
- Acid protonates the carbamate
- The tert-butyl group leaves as a cation
- Carbon dioxide leaves and the amine is free
Try it on your own structures
Enter your reactants in the Reaction Lab. If this transformation matches what you drew, it is applied and the outcome is shown next to the records that back it — with the count of documented reactions doing the same thing on substrates like yours, rather than a confidence score.
Other deprotection transformations
Cbz removed from an amine
Hydrogen over a metal cleaves the benzyl carbamate, leaving the free amine.
Benzyl ether removed
Hydrogen over a metal cleaves the benzyl ether, leaving the alcohol.
Silyl ether removed
Fluoride cleaves the silicon–oxygen bond, leaving the alcohol.
Fmoc removed from an amine
A secondary amine takes the acidic hydrogen and the group falls away.
Demethylation of an aryl methyl ether
The methyl is taken off an aromatic methyl ether, leaving the phenol.