(Boc)2NH CAS 51779-32-9 Di-tert-Butyl Iminodicarboxylate Purity >99.0% (HPLC) Factory Protecting Reagent

Di-tert-Butyl Iminodicarboxylate ((Boc)2NH) (CAS: 51779-32-9)
Application Di-tert-Butyl Iminodicarboxylate is a pharmaceutical intermediate, which can be prepared by one-step reaction of formamide and Boc2O.  
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.
Di-tert-Butyl Iminodicarboxylate is a protected amine group that is used to prepare conformationally constrained spirocycles as CCR1 antagonists.
Preparation the solution of DMAP (0.61g, 5.0mmol) in MeCN (15ml) is slowly added to the solution of formamide (2.5g,56mmol) and Boc2O (24g, 110mol) in MeCN (15ml). After stirring at room temperature for 4h, the yellow solution was cooled to 0°C, and N,N-diethylenediamine (6.97g, 60mmol) was slowly added at 0℃. The resulting mixture was stirred at room temperature for 12h and filtered through a thin silica pad; the resulting mixture was filtered at room temperature. The solvent is then evaporated under reduced pressure. The crude product was purified by silica gel chromatography and eluted with EtOAc/hexane (1:5) to obtain the title product, which is a white solid (10.99g, 92%).