73831-40-0Relevant academic research and scientific papers
(±)-cis-2-Methyl-4-oxocyclohexane-carboxylic acid: Catemeric hydrogen bonding in a δ-keto acid derived from Hagemann's ester
Lalancette, Roger A.,Thompson, Hugh W.
, p. o679-o681 (2003)
The crystallization of (±)-cis-2-methyl-4-oxocyclohexanecarboxylic acid as acid-to-ketone hydrogen-bonding catemers was investigated. It was stated that in either chair conformation for the compound, one of the two cis-related susbstituents must be axial. The hydrogen bonds progress from the carboxyl group of each molecule to the ketone group of a translationaly related neighbor. It was found that three intermolecular C-H···O close contacts exist involving both carboxyl O atoms. The peak separation conforms to the shifts observed in catemers, due to removal of hydrogen bonding from the acid C=O group and addition of hydrogen bonding to the ketone group.
Asymmetric Synthesis of the Cyclohexyl Fragment in RORγt Inhibitor (BMS-986251) Enabled by a Dynamic Kinetic Resolution of Hageman's Ester
Coombs, John R.,Gallagher, William P.,González-Bobes, Francisco,Guerrero, Carlos A.,Joe, Candice L.,Katipally, Kishta,Mudryk, Boguslaw M.,Rupasinghe, Sanjeewa,Zhu, Jason
, (2021/11/30)
The cyclohexyl fragment 1 in BMS-986251 was synthesized starting from Hagemann's ester 2 in 7 steps and 5 isolations. The route is highlighted by a dynamic kinetic resolution (DKR), a telescoped enol nonaflation followed by a palladium-catalyzed carbonylation, and a rhodium-catalyzed directed diastereoselective olefin hydrogenation. The optimized process was demonstrated on 1 kg scale, with an overall 51% yield and >99% ee and dr.
Development of a Scalable Synthetic Route to BMS-986251. Part 1: Synthesis of the Cyclohexane Dicarboxylate Fragment
Coombs, John R.,Eastgate, Martin D.,Gallagher, William P.,Gangu, Aravind S.,Gonzalez-Bobes, Francisco,Joe, Candice L.,Kalidindi, Srinivas,Kopp, Nathaniel,Kuppusamy, Sankar,Mudryk, Boguslaw,Nagappan, Vedhachalam,Palani, Senthil,Ponnusamy, Muthukrishnan,Rupasinghe, Sanjeewa,Tendulkar, Shankar,Vaidyanathan, Rajappa,Venu, Alla,Vinodini, Arun
, p. 1547 - 1555 (2021/07/19)
The cyclohexane dicarboxylate unit of BMS-986251 (1), a potent and efficacious RORγt inverse agonist, was synthesized starting from Hagemann's ester in seven chemical transformations with five isolated intermediates. The synthesis involved an enzymatic ki
Enantioselective synthesis of the hexahydronaphthalene nucleus of (-)-compactin from ethyl (1R,2S)-2-methyl-4-oxocyclohexanecarboxylate and 2-(3-nitropropyl)-1,3-dioxolane as four carbon bifunctional annelating agent
Barco,Benetti,Bianchi,Casolari,Pollini,Romagnoli,Spalluto,Zanirato
, p. 11743 - 11754 (2007/10/02)
An enantioselective approach to the synthesis of the hexahydronaphthalene nucleus of natural compactin is described. The key elements of the synthesis are as follows: (i) the preparation of the chiral starting material through enzymatic resolution of the
