Di-tert-butyl iminodicarboxylate

Synthesis

A solution of DMAP (0.61 g, 5.0 mmol) in MeCN (15 ml) was slowly added to a solution of formamide (2.5 g, 56 mmol) and Boc2O (24 g, 110 mol) in MeCN (15 ml). After stirring at room temperature for 4 h, the yellow solution was cooled to 0 °C, and N,N-diethylethylenediamine (6.97 g, 60 mmol) was slowly added at 0 °C. The resulting mixture was stirred at room temperature for 12 h and filtered through a silica mat; the resulting mixture was then filtered at room temperature. The solvent was then evaporated under reduced pressure. The crude product was purified by silica gel chromatography, eluted with EtOAc/hexane (1:5) to give the title product as a white solid (10.99 g, 92%).

Uses

Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH3)3COC(O)]2NH. It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides. 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. 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.

Chemical Properties

White to beige crystalline powder

Uses

Di-tert-butyl iminodicarboxylate is a protected amine group that is used to prepare conformationally constrained spirocycles as CCR1 antagonists.