206446-48-2

Basic information

• Product Name: tert-butyl 4-(4-(ethoxycarbonyl)phenyl)piperidine-1-carboxylate
• Synonyms: tert-butyl 4-(4-(ethoxycarbonyl)phenyl)piperidine-1-carboxylate
• CAS NO: 206446-48-2
• Molecular Formula: C19H27NO4
• Molecular Weight: 333.42198
• Mol File: 206446-48-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 439.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.099±0.06 g/cm3(Predicted)
• PKA: -1.82±0.40(Predicted)
• CAS DataBase Reference: tert-butyl 4-(4-(ethoxycarbonyl)phenyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-(4-(ethoxycarbonyl)phenyl)piperidine-1-carboxylate(206446-48-2)
• EPA Substance Registry System: tert-butyl 4-(4-(ethoxycarbonyl)phenyl)piperidine-1-carboxylate(206446-48-2)

Safety Data

• Hazardous Substances Data: 206446-48-2(Hazardous Substances Data)

Upstream product

• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 1240969-31-6 4-(4-ethoxycarbonylphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 4334-88-7 p-ethoxycarbonylphenylboronic acid 
• 159503-91-0 tert-butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 

Relevant articles and documents

Micelle enabled C(sp2)-C(sp3) cross-electrophile coupling in waterviasynergistic nickel and copper catalysis

A robust and sustainable C(sp2)-C(sp3) cross-electrophile coupling was developedvianickel/copper synergistic catalysis under micellar conditions. This protocol provided a general method to access alkylated arenes with good to excellent yields on a very large scale.

General C(sp2)-C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts

Cross-electrophile coupling (XEC) of alkyl and aryl halides promoted by electrochemistry represents an attractive alternative to conventional methods that require stoichiometric quantities of high-energy reductants. Most importantly, electroreduction can readily exceed the reducing potentials of chemical reductants to activate catalysts with improved reactivities and selectivities over conventional systems. This work details the mechanistically-driven development of an electrochemical methodology for XEC that utilizes redox-active shuttles developed by the energy-storage community to protect reactive coupling catalysts from overreduction. The resulting electrocatalytic system is practical, scalable, and broadly applicable to the reductive coupling of a wide range of aryl, heteroaryl, or vinyl bromides with primary or secondary alkyl bromides. The impact of overcharge protection as a strategy for electrosynthetic methodologies is underscored by the dramatic differences in yields from coupling reactions with added redox shuttles (generally >80%) and those without (generally 20%). In addition to excellent yields for a wide range of substrates, reactions protected from overreduction can be performed at high currents and on multigram scales.

Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile

While reductive cross-electrochemical coupling is an attractive approach for the synthesis of complex molecules at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a divided electrochemical cell using acetonitrile as the solvent and diisopropylamine as the sacrificial reductant to afford coupling products in synthetically useful yields (22-80%). Additionally, the use of a combination of the ligands 4,4′,4″-tri-tert-butyl-2,2′:6′,2′-terpyridine and 4,4′-di-tert-butyl-2,2′-bipyridine is essential to achieve high yields.