1,1'-(Azodicarbonyl)-dipiperidine

Description

1,1''-(Azodicarbonyl)dipiperidine (ADDP) is a reagent commonly used in the Mitsunobu reaction for the condensation of an alcohol and an acidic compound. It has been used as a reagent in the synthesis of G protein-coupled receptor 120 (GPR120) agonists with antidiabetic activity and peroxisome proliferator-activated receptor α (PPARα), PPARγ, and PPARδ triple agonists.

Description

Azo-type reagents are poorer Michael acceptors than DEAD, therefore they are generally paired with more nucleophilic phosphine reagents than TPP, such as tributylphosphine or trioctylphosphine.

Chemical properties

yellow crystalline powder

The Uses of 1,1'-(Azodicarbonyl)-dipiperidine

It is used in a study of the copper-catalyzed addition of aryboronic acids to azodicarboxyl derivatives providing aryl-substituted hydrazides. It is widely used reagent for the Mitsunobu reaction. It is reactant for preparation of polyfluoroalkylated tripyrazolylmethane ligands, (-)-Hygromycin A via Mitsunobu glycosylation, optically active α,α-disubstituted amino acids via Mitsunobu reaction, aza-β-lactams through [2+2] cycloaddition reactions, glycosyl disulfides, pyridine ether PPAR agonists, S-glycosyl amino acid, building blocks for combinatorial neoglycopeptide synthesis and is a histamine H3 receptor antagonists. It is a reactant for Mitsunobu inversion reactions.

The Uses of 1,1'-(Azodicarbonyl)-dipiperidine

To a solution of A (400 mg, 1.54 mmol), B (621 mg, 3.09 mmol), and PPh3 (610 mg, 2.32 mmol) in THF (5.5 mL) at RT was added DEAD (404 mg, 2.32 mmol) in THF (0.5 mL). After 90 min, silica gel was added and the mixture was concentrated and purified on a flash column (25% EtOAc/hexane) to provide the product. [545 mg, 80%]

What are the applications of Application

1,1′-(Azodicarbonyl)dipiperidine is a commonly used reagent for the Mitsunobu reaction