180695-79-8

Usage

Uses

Used in Pharmaceutical Synthesis:
1-N-BOC-4-BROMOPIPERIDINE is used as a key intermediate for the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the creation of a wide range of bioactive molecules and pharmaceutical ingredients, contributing to the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1-N-BOC-4-BROMOPIPERIDINE is utilized as a precursor in the preparation of compounds with potential therapeutic applications. Its presence in the molecular structure can influence the pharmacological properties of the resulting compounds, making it a valuable tool in the discovery and design of novel drugs.
Used in Organic Synthesis:
1-N-BOC-4-BROMOPIPERIDINE serves as a versatile building block in organic synthesis, enabling the construction of complex organic molecules. Its reactivity and functional groups make it suitable for various synthetic routes, facilitating the production of a diverse array of organic compounds for different applications.

InChI:InChI=1/C10H18BrNO2/c1-10(2,3)14-9(13)12-6-4-8(11)5-7-12/h8H,4-7H2,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 54288-70-9 4-bromopiperidine hydrobromide 
• 90633-18-4 4-bromo-1H-piperidine 
• 558-13-4 carbon tetrabromide 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 24608-52-4 tert-butyl chloroformate 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Downstream Products

• 769159-61-7 4-[5-cyano-2-(3,5-dichloro-phenoxy)-phenylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 159503-92-1 tert-butyl 4-(benzylsulfanyl)piperidine-1-carboxylate 
• 333985-88-9 tert-butyl 4-(pyridin-2-ylthio)piperidine-1-carboxylate 
• 442198-32-5 (2E)-3-(4-Chlorophenyl)-N-[(1S)-2-oxo-2-({2-oxo-2-[4-(3-pyridyloxy)-1-piperidinyl]ethyl}amino)-1-(2-pyridylmethyl)ethyl]-acrylamide 
• 333954-87-3 tert-butyl 4-[(4-chlorophenyl)thio] piperidine-1-carboxylate 
• 333986-94-0 4-(4-nitrophenylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester 
• 690261-78-0 tert-butyl 4-(thiophen-3-yl)piperidine-1-carboxylate 
• 201609-29-2 1-t-Butoxycarbonyl-4-(2-methoxyphenyl)piperidine 
• 183950-95-0 tert-butyl 4-(4'-fluorophenyl)piperidine-1-carboxylate 
• 1612155-93-7 tert-butyl 4-(4-acetamidophenyl)piperidine-1-carboxylate 
• 256381-04-1 tert-butyl 4-(4-acetylphenyl)piperidine-1-carboxylate 
• 550371-77-2 tert-butyl 4-(pyridin-3-yl)piperidine-1-carboxylate 
• 1462849-53-1 tert-butyl 4-(2-methylpyridin-3-yl)piperidine-1-carboxylate 
• 1612156-05-4 tert-butyl 4-(3-(1H-pyrazol-5-yl)phenyl)piperidine-1-carboxylate 

Relevant academic research and scientific papers

4-Hydroxy-1,2,3-triazole moiety as bioisostere of the carboxylic acid function: a novel scaffold to probe the orthosteric γ-aminobutyric acid receptor binding site

The correct application of bio(iso)steric replacement, a potent tool for the design of optimized compounds, requires the continuous development of new isosters able to respond to specific target requirements. Among carboxylic acid isosters, as the hydroxy

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.

Reductive Radical Conjugate Addition of Alkyl Electrophiles Catalyzed by a Cobalt/Iridium Photoredox System

Alkyl and aryl halides have been studied extensively as radical precursors; however, mild and less toxic conditions for the activation of alkyl bromides toward alkyl radicals are still desirable. Reported here is a reductive radical conjugate addition tha

Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents

The development of a copper-catalyzed cross-coupling between primary and secondary (pseudo)halides and bicyclopentyl Grignard reagents is reported. Highly strained bicyclopentanes can be cross-coupled with a large panel of primary alkyl mesylates and secondary alkyl iodides. The catalytic system is simple and cheap, and the reaction is general and chemoselective.

Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation

An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen sources (NaBr, NaI, or HCl), to yield an alkyl halide. Because of the mild conditions, a wide range of functional groups were tolerated, and excellent site selectivity was achieved.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Palladium-Catalyzed Alkoxycarbonylation of Unactivated Secondary Alkyl Bromides at Low Pressure

Catalytic carbonylations of organohalides are important C-C bond formations in chemical synthesis. Carbonylations of unactivated alkyl halides remain a challenge and currently require the use of alkyl iodides under harsh conditions and high pressures of CO. Herein we report a palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides that proceeds at low pressure (2 atm CO) under mild conditions. Preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. These reactions efficiently deliver esters from unactivated alkyl bromides across a diverse range of substrates and represent the first catalytic carbonylations of alkyl bromides with carbon monoxide.

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.

Iron-catalyzed borylation of alkyl, allyl, and aryl halides: Isolation of an iron(I) boryl complex

Activation of B2pin2 with tBuLi facilitates the Fe-catalyzed borylation of alkyl, allyl, benzyl, and aryl halides via the formation of Li[B2pin2(tBu)] (1). The reaction of 1 with a representative iron phosphine precatalyst generates the unique iron(I) boryl complex [Fe(Bpin)(dpbz)2] (2).

Compounds Which Selectively Modulate The CB2 Receptor

Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.