651053-90-6

Upstream product

• 16419-60-6 2-Methylphenylboronic acid 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 1028273-34-8 4-o-tolyl-4H-pyridine-1-carboxylic acid tert-butyl ester 
• 110-86-1 pyridine 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 932-31-0 ortho-tolylmagnesium bromide 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 651053-67-7 4-o-tolyl-4H-pyridine-1-carboxylic acid phenyl ester 

Downstream Products

• 630116-52-8 4-(2'-methylphenyl)piperidine 

Relevant academic research and scientific papers

Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents

A cobalt-catalyzed cross-coupling between 3- and 4-iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)-preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates. Scaffold synthesis: A cobalt-catalyzed cross-coupling between iodopiperidines and Grignard reagents is reported (see scheme; PG=protecting group). A large variety of 3- and 4-substituted piperidines were synthesized and the method was applied to a short synthesis of (±)-preclamol. This work constitutes one of the rare examples of cross-couplings involving 3-halogeno piperidines.

Efficient Solution-Phase Parallel Synthesis of 4-Substituted N-Protected Piperidines

Practical conditions for the synthesis of 4-substituted N-protected piperidines through CuCN·2LiBr-catalyzed organozinc additions to 1-acylpyridinium salts and subsequent hydrogen-transfer hydrogenation have been established. The reaction sequence is performed at room temperature and provides 4-substituted N-protected piperidines in excellent overall yields without the isolation of intermediate dihydropyridines, In those cases in which the organozinc addition results in mixtures of 2- and 4-substituted dihydropyridines, the 2-substituted isomers are efficiently scavenged with maleic anhydride and subsequently removed by a mild extractive workup with NaHCO3 (sat.). The N-acyl group can conveniently be exchanged from N-phenoxycarbonyl to N-tBoc, thus allowing orthogonal deprotection strategies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Serine derived NK1 antagonists 2: A pharmacophore model for arylsulfonamide binding

Modifications to the spirocyclic aryl sulfonamide portion of serine derived NK1 antagonists allow a partial pharmacophore model to be developed.