123387-49-5

Basic information

• Product Name: tert-butyl 4-phenylpiperidine-1-carboxylate
• Synonyms: tert-butyl 4-phenylpiperidine-1-carboxylate;tert-Butyl 4-phenylpiperidin-1-carboxylate;1-Piperidinecarboxylic acid, 4-phenyl-, 1,1-diMethylethyl ester;"4-phenyl-1-Piperidinecarboxylic acid 1,1-diMethylethyl ester
• CAS NO: 123387-49-5
• Molecular Formula: C₁₆H₂₃NO₂
• Molecular Weight: 261.35932
• Mol File: 123387-49-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-butyl 4-phenylpiperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-phenylpiperidine-1-carboxylate(123387-49-5)
• EPA Substance Registry System: tert-butyl 4-phenylpiperidine-1-carboxylate(123387-49-5)

Safety Data

• Hazardous Substances Data: 123387-49-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl 4-phenylpiperidine-1-carboxylate is used as a chemical intermediate for the synthesis of biologically active compounds. Its piperidine ring structure may contribute to central nervous system activity, which is valuable for the development of analgesic or antipsychotic drugs. The tert-butyl ester group enhances the compound's stability and pharmacokinetic properties, improving its potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, tert-butyl 4-phenylpiperidine-1-carboxylate serves as a key component in the design and synthesis of new pharmaceuticals. Its structural elements are manipulated to explore and enhance the compound's efficacy and safety, aiming to create novel drugs with improved pharmacological profiles for the treatment of various conditions.

InChI:InChI=1S/C16H23NO2/c1-16(2,3)19-15(18)17-11-9-14(10-12-17)13-7-5-4-6-8-13/h4-8,14H,9-12H2,1-3H3

Upstream product

• 368-47-8 phenyltrifluorosilane 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 771-99-3 4-phenylpiperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 108-86-1 bromobenzene 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 100-59-4 phenylmagnesium chloride 
• 100-58-3 phenylmagnesium bromide 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 1078-58-6 diphenylzinc 
• 1309607-10-0 bromo({1-[(tert-butoxy)carbonyl]piperidin-4-yl})zinc 
• 108-90-7 chlorobenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 126503-18-2 (1S,7R,8aS)-1,7-Diphenyl-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 126503-17-1 (2R,4S)-2-((S)-Hydroxy-phenyl-methyl)-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 123387-61-1 2-Allyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 123387-60-0 (2R,4R)-2-Methyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 123387-60-0 2-Methyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 261777-38-2 (2R,4S)-cis-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 261777-44-0 (2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester 
• 261777-41-7 (2R,4S)-cis-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester 
• 126503-25-1 (2R,6R)-2,6-Dimethyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 88131-88-8 erythro-2(e)-(α-hydroxybenzyl)-4-phenylpiperidine 
• 126503-23-9 (2R,4R,6S)-2-((R)-Hydroxy-phenyl-methyl)-6-methyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 126503-23-9 (2R,4R,6S)-2-((S)-Hydroxy-phenyl-methyl)-6-methyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 766513-26-2 C₁₆H₂₁NO₃ 
• 1241505-11-2 tert-butyl 2-(3-oxocyclohexyl)-4-phenylpiperidine-1-carboxylate 

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.

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides

As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

Modulators of protease activated receptors

The present invention provides novel compounds of the Formula (I), pharmaceutical compositions comprising such compounds and methods for using such compounds as tools for biological studies or as agents or drugs for therapies such as metabolic syndrome, obesity, type II diabetes, fibrosis and cardiovascular diseases, whether they are used alone or in combination with other treatment modalities.

Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow

An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp3)-C(sp2) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process.

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

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.

Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids

A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2?6 H2O—$9.5 mol?1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.

Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents

Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, we demonstrate that TDAE addition can be used as a control element to ‘hold’ a reaction without diminishing yield or catalyst activity.