Di-tert-butyl-iminodicarboxylate

Di-<i>tert</i>-butyl-iminodicarboxylate

Di-tert-butyl-iminodicarboxylate

Chemical compound

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.[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]

Quick Facts Names, Identifiers ...

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.

References

  1. [1]
    Ulf Ragnarsson; Leif Grehn (1991). "Novel Gabriel Reagents". Acc. Chem. Res. 24 (10): 285–289. doi:10.1021/ar00010a001.
  2. [2]
    Neelamkavil, Santhosh "Di-tert-butyl-imidocarbonate" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. doi:10.1002/047084289X.rn00488
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