Di-tert-butyl-iminodicarboxylate

The compound is used as a reagent for the preparation of primary amines from alkyl halides.

[1] It was popularized as an alternative to the Gabriel synthesis for the same conversion.

Amines can also be prepared from alcohols by dehydration using the Mitsunobu reaction.

[2] In the usual implementation the reagent is deprotonated to give the potassium salt, which is N-alkylated.

The Boc protecting groups are subsequently removed under acidic conditions.