1276045-26-1

Basic information

• Product Name: 4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester
• Synonyms: 4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester
• CAS NO: 1276045-26-1
• Molecular Weight: 291.39
• Mol File: 1276045-26-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester(1276045-26-1)
• EPA Substance Registry System: 4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester(1276045-26-1)

Safety Data

• Hazardous Substances Data: 1276045-26-1(Hazardous Substances Data)

Upstream product

• 1003858-50-1 2-(3-methoxyphenyl)-5, 5-dimethyl-1,3,2-dioxaborinane 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 2398-37-0 3-methoxyphenyl bromide 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 1309607-10-0 bromo({1-[(tert-butoxy)carbonyl]piperidin-4-yl})zinc 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 766-85-8 3-methoxy-1-iodobenzene 
• 194669-45-9 4-(3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 99329-55-2 4-(3-methoxyphenyl)piperidine 
• 1276045-01-2 2-ethyl-1-[4-(3-methoxy-phenyl)-piperidin-1-yl]-butan-1-one 
• 1276045-02-3 1-(4-(3-methoxyphenyl)piperidin-1-yl)-3-methylbutan-1-one 
• 1276045-03-4 cyclopropyl-[4-(3-methoxy-phenyl)-piperidin-1-yl]-methanone 
• 1276045-04-5 [4-(3-methoxy-phenyl)-piperidin-1-yl]-(2-methyl-cyclopropyl)-methanone 
• 1276045-05-6 (2,2-dimethyl-cyclopropyl)-[4-(3-methoxy-phenyl)-piperidin-1-yl]-methanone 
• 1276045-06-7 cyclobutyl(4-(3-methoxyphenyl)piperidin-1-yl)methanone 
• 1276045-07-8 cyclopentyl(4-(3-methoxyphenyl)piperidin-1-yl)methanone 
• 1276045-08-9 cyclohexyl(4-(3-methoxyphenyl)piperidin-1-yl)methanone 
• 1276045-09-0 [4-(3-methoxy-phenyl)-piperidin-1-yl]-phenyl-methanone 
• 1276045-10-3 cyclopropyl-[4-(3-ethoxy-phenyl)-piperidin-1-yl]-methanone 
• 1276045-12-5 cyclopropyl-[4-(3-hydroxy-phenyl)-piperidin-1-yl]-methanone 
• 1276045-17-0 C₁₄H₁₉NO₃ 
• 1276044-98-4 1-[4-(3-methoxy-phenyl)-piperidin-1-yl]-ethanone 

Relevant articles and documents

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands

Cobalt(II) halides in combination with phenoxyimine (FI) ligands generated efficient precatalysts in situ for the C(sp2)-C(sp3) Suzuki-Miyaura cross-coupling between alkyl bromides and neopentylglycol (hetero)arylboronic esters. The protocol enabled efficient C-C bond formation with a host of nucleophiles and electrophiles (36 examples, 34-95%) with precatalyst loadings of 5 mol %. Studies with alkyl halide electrophiles that function as radical clocks support the intermediacy of alkyl radicals during the course of the catalytic reaction. The improved performance of the FI-cobalt catalyst was correlated with decreased lifetimes of cage-escaped radicals as compared to those of diamine-type ligands. Studies of the phenoxyimine-cobalt coordination chemistry validate the L,X interaction leading to the discovery of an optimal, well-defined, air-stable mono-FI-cobalt(II) precatalyst structure.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

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.