303975-71-5

Basic information

• Product Name: tert-butyl 4-(4-methoxyphenyl)piperidine-1-carboxylate
• Synonyms: tert-butyl 4-(4-methoxyphenyl)piperidine-1-carboxylate
• CAS NO: 303975-71-5
• Molecular Weight: 291.39
• Mol File: 303975-71-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: tert-butyl 4-(4-methoxyphenyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-(4-methoxyphenyl)piperidine-1-carboxylate(303975-71-5)
• EPA Substance Registry System: tert-butyl 4-(4-methoxyphenyl)piperidine-1-carboxylate(303975-71-5)

Safety Data

• Hazardous Substances Data: 303975-71-5(Hazardous Substances Data)

Upstream product

• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 149377-19-5 4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 74-88-4 methyl iodide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 1510865-53-8 tert-butyl 4-(2-((4-methoxyphenyl)sulfonyl)hydrazono)piperidine-1-carboxylate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 1046478-89-0 tert-butyl 4-(p-tolylsulfonylhydrazono)-piperidine-1-carboxylate 
• 138647-51-5 4-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 66107-29-7 4-methoxyphenyl triflate 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 

Downstream Products

• 67259-62-5 4-(4-methoxyphenyl)piperidine 
• 6748-48-7 4-(4-methoxyphenyl)-piperidinehydrochloride 
• 1276045-16-9 1-[4-(4-methoxy-phenyl)-piperidin-1-yl]-ethanone 
• 1276045-15-8 cyclopropyl-[4-(4-methoxy-phenyl)-piperidin-1-yl]-methanone 
• 62614-84-0 4-(4-hydroxyphenyl)-1,2,3,6-tetrahydropiperidine 

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.

Design, Synthesis, and Pharmacological Characterization of Heterobivalent Ligands for the Putative 5-HT2A/mGlu2Receptor Complex

We report the synthesis of the first series of heterobivalent ligands targeting the putative heteromeric 5-HT2A/mGlu2 receptor complex, based on the 5-HT2A antagonist MDL-100,907 and the mGlu2 ago-PAM JNJ-42491293. The functional properties of monovalent and heterobivalent ligands were characterized in 5-HT2A-, mGlu2/Gqo5-, 5-HT2A/mGlu2-, and 5-HT2A/mGlu2/Gqo5-expressing HEK293 cells using a Ca2+ imaging assay and a [3H]ketanserin binding assay. Pronounced functional crosstalk was observed between the two receptors in 5-HT2A/mGlu2 and 5-HT2A/mGlu2/Gqo5 cells. While the synthesized monovalent ligands retained the 5-HT2A antagonist and mGlu2 ago-PAM functionalities, the seven bivalent ligands inhibited 5-HT-induced responses in 5-HT2A/mGlu2 cells and both 5-HT- and Glu-induced responses in 5-HT2A/mGlu2/Gqo5 cells. However, no definitive correlation between the functional potency and spacer length of the ligands was observed, an observation substantiated by the binding affinities exhibited by the compounds in 5-HT2A, 5-HT2A/mGlu2, and 5-HT2A/mGlu2/Gqo5 cells. In conclusion, while functional crosstalk between 5-HT2A and mGlu2 was demonstrated, it remains unclear how these heterobivalent ligands interact with the putative receptor complex.

Practical synthesis of pharmaceutically relevant molecules enriched in sp3 character

The expedient synthesis of compounds enriched in sp3 character is key goal in modern drug discovery. Herein, we report how a single pot Suzuki-Miyaura-hydrogenation can be used to furnish lead and fragment-like products in good to excellent yields. The approach has been successfully applied in formats amenable to parallel synthesis, in an asymmetric sense, and in the preparation of molecules with annotated biological activity.