Di-tert-butyl-iminodicarboxylate
Names
Preferred IUPAC name
Di-tert-butyl 2-imidodicarbonate
Other names
HN(Boc)2; Bis-Boc amine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C10H19NO4/c1-9(2,3)14-7(12)11-8(13)15-10(4,5)6/h1-6H3,(H,11,12,13)
    Key: XCAQIUOFDMREBA-UHFFFAOYSA-N
  • CC(C)(C)OC(=O)NC(=O)OC(C)(C)C
Properties
C10H19NO4
Molar mass 217.265 g·mol−1
Appearance White solid
Melting point 119–121 °C (246–250 °F; 392–394 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

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. ↑ Ulf Ragnarsson; Leif Grehn (1991). "Novel Gabriel Reagents". Acc. Chem. Res. 24 (10): 285–289. doi:10.1021/ar00010a001.
  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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