Di-tert-butyl-iminodicarboxylate

Di-*tert*-butyl-iminodicarboxylate
Names
	Preferred IUPAC name Di-tert-butyl 2-imidodicarbonate
	Other names HN(Boc)2; Bis-Boc amine
Identifiers
CAS Number	51779-32-9;
3D model (JSmol)	Interactive image;
ChemSpider	246393;
PubChem CID	279800;
UNII	85M4Q7458H ;
CompTox Dashboard (EPA)	DTXSID70299500 ;
	InChI 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;
	SMILES CC(C)(C)OC(=O)NC(=O)OC(C)(C)C;
Properties
Chemical formula	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

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

[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

[1]

[2]