287729-00-4

Upstream product

• 34387-89-8 N-(tert-butoxycarbonylamino)phthalimide 
• 100-39-0 benzyl bromide 
• 85-44-9 phthalic anhydride 
• 220294-77-9 N^β,N^β-[bis(tert-butoxycarbonyl)amino]phthalimide 
• 1875-48-5 N-aminophthalamide 
• 870-46-2 t-butoxycarbonylhydrazine 
• 100-51-6 benzyl alcohol 
• 215655-64-4 1-tert-butyloxycarbonyl-2-(2'-carboxybenzoyl)-hydrazine 
• 109473-36-1 N-tert-butyloxycarbonylaminoisophthalimide 

Downstream Products

• 147688-34-4 tert-butyl 1-benzylhydrazine-1-carboxylate 
• 185456-32-0 1-benzyl-1,2,2-tris(tert-butoxycarbonyl)hydrazine 
• 127799-53-5 1-[(1,1-dimethylethoxy)carbonyl]-2-[(phenylmethoxy)carbonyl]-2-methylhydrazine 
• 85468-51-5 2-benzylamino-1H-isoindole-1,3(2H)-dione 
• 1073-62-7 N-benzylhydrazine hydrochloride 
• 185456-43-3 N-benzyl-N’-[(tert-butoxy)carbonyl](tert-butoxy)carbohydrazide 

Relevant academic research and scientific papers

Original and efficient synthesis of 2:1-[α/aza]-oligomer precursors

The preparation of 2:1-[α/aza]-oligomer precursors is described via Mitsunobu and exchange of protecting groups protocols in four steps in good yields starting from N-tert-butyloxycarbonylaminophtalimide. Conformational studies showed that these building blocks further led to β-turn-like folded 2:1-[α/aza]-trimer which suggests that they are good candidates to form foldamers.

Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches

Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N-aminophthalimide derivatives can be efficiently converted into the corresponding N-amino-imidodicarbonates by a three-stage, one-flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ -diprotected α-hydrazino esters. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

N-tert-butoxycarbonylaminophthalimide, a versatile reagent for the conversion of alcohols into alkylated tert-butylcarbazates or hydrazines via the Mitsunobu protocol

An efficient two-step method has been developed for the conversion of alcohols to substituted hydrazines. The use of N-tert- butoxycarbonylaminophthalimide as an acid partner in Mitsunobu reactions with a variety of alcohols permits the synthesis of the corresponding monoalkylated tert-butylcarbazates and hydrazines.

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pKa values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.