1,1'-(Azodicarbonyl)dipiperidine (Synonyms: ADDP, NSC 356027)

1,1'-(Azodicarbonyl)dipiperidine (ADDP) is a reagent commonly used in the Mitsunobu reaction for the condensation of an alcohol and an acidic compound.^1,2 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.^3,4

1.Tsunoda, T., Yamamiya, Y., and ItÔ, S.1,1′-(Azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for Mitsunobu reactionTetrahedron Lett.34(10)1639-1642(1993) 2.Hirose, D., Gazvoda, M., Košmrlj, J., et al.Systematic evaluation of 2-arylazocarboxylates and 2-arylazocarboxamides as Mitsunobu reagentsJ. Org. Chem.83(8)4712-4729(2018) 3.Zhang, X., Cai, C., Winters, M., et al.Design, synthesis and SAR of a novel series of heterocyclic phenylpropanoic acids as GPR120 agonistsBioorg. Med. Chem. Lett.27(15)3272-3278(2017) 4.Mogensen, J.P., Jeppesen, L., Bury, P.S., et al.Design and synthesis of novel PPARα/γ/δ triple activators using a known PPARα/γ dual activator as structural templateBioorg. Med. Chem. Lett.13(2)257-260(2003)