55581-65-2

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General Description

1-Pivaloylpiperidine, also known as N-tert-butylpiperidine-3-carboxylic acid, is a chemical compound with the molecular formula C12H23NO2. It is a piperidine derivative with a bulky tert-butyl group attached to the nitrogen atom. This chemical is known for its use in the synthesis of various pharmaceutical compounds and is also used as an intermediate in organic synthesis. 1-Pivaloylpiperidine has been studied for its potential application in the development of new drugs due to its diverse pharmacological properties. It is important to handle this chemical with caution as it may pose health and environmental risks if not handled properly. Overall, 1-Pivaloylpiperidine is a versatile chemical that has various applications in the pharmaceutical and chemical industries.

Upstream product

• 110-89-4 piperidine 
• 3282-30-2 pivaloyl chloride 
• 138963-93-6 Thiopivalinsaeure-O-methylester 
• 75-98-9 Trimethylacetic acid 
• 558-17-8 tert-Butyl iodide 
• 13939-06-5 molybdenum hexacarbonyl 
• 630-19-3 pivalaldehyde 

Relevant academic research and scientific papers

Conformational study on 2-acyl-1-alkylidene-1,2,3,4-tetrahydroisoquinolines

The title enamide compounds can exist in either a sickle or U conformation with respect to the C=C-N-C=C conjugated moiety, where the sickle form is greatly favored. The sickle rotamers are chiral in nature in both solution and crystalline states, as prov

Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines

A one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible, and abundant reagents.

DECONSTRUCTIVE FUNCTIONALIZATION METHODS AND COMPOUNDS

Disclosed herein, inter alia, are deconstructive functionalization methods and compounds made using the same.

Ligand-Enabled Enantioselective Csp3 –H Activation of Tetrahydroquinolines and Saturated Aza-Heterocycles by RhI

The first rhodium(I)-catalyzed enantioselective intermolecular C (Formula presented.) –H activation of various saturated aza-heterocycles including tetrahydroquinolines, piperidines, piperazines, azetidines, pyrrolidines, and azepanes is presented. The combination of a rhodium(I) precatalyst and a chiral monodentate phosphonite ligand is shown to be a powerful catalytic system to access a variety of important enantio-enriched heterocycles from simple starting materials. Notably, the C (Formula presented.) –H activation of tetrahydroquinolines is especially challenging due to the adjacent C (Formula presented.) ?H bond. This redox-neutral methodology provides a new synthetic route to α-N-arylated heterocycles with high chemoselectivity and enantioselectivity up to 97 % ee.

Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas

A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.

Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)?H Bonds

A mild, oxidant-free, and selective Cp*CoIII-catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp3)?H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C?H amidation of a wide range of functionalized thioamides with aryl-, heteroaryl-, and alkyl-substituted dioxazolones under the Cp*CoIII-catalyzed conditions. The observed regioselectivity towards primary C(sp3)?H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate-assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*CoIII-catalyzed C(sp3)?H functionalization and the first to exploit thioamides.

Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis

A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.

Low-Pressure Radical11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation

A radical11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated11C-aminocarbonylation, which is limited to the preparation of11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

Mild and selective Et2Zn-catalyzed reduction of tertiary amides under Hydrosilylation conditions

Diethylzinc (Et2Zn) can be used as an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing cost-effective polymeric silane (PMHS) as the hydride source. Crucial for the catalytic activity was the addition of a substoichiometric amount of lithium chloride to the reaction mixture. A series of amides containing different additional functional groups were reduced to their corresponding amines, and the products were isolated in good-to-excellent yields.

α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling

Pd(II)-catalyzed α-C(sp3)-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.