Fmoc removed from an amine
A secondary amine takes the acidic hydrogen and the group falls away.
What it needs, and what it gives
- Reaction class
- Deprotection
- Piperidine. Acid does not remove it, which is the point.
- not stated
- Mechanism
- Base removal of an Fmoc group, 3 steps
How it is thought to happen
The base takes a hydrogen the fluorene ring makes unusually acidic, the carbamate is pushed out, and what is left gives off carbon dioxide.
- The base takes the acidic hydrogen
- The carbamate is pushed out
- 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
Boc removed from an amine
Acid takes the carbamate off, leaving the free amine.
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.
Demethylation of an aryl methyl ether
The methyl is taken off an aromatic methyl ether, leaving the phenol.