3742-91-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzyl piperidine-1-carboxylate is utilized as a key intermediate in the organic synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of a broad range of medications, contributing to the development of new treatments and therapies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, benzyl piperidine-1-carboxylate is employed as a building block for the design and synthesis of new drug candidates. Its presence in these compounds can influence their pharmacological properties, making it a valuable component in the quest for novel therapeutic agents.
Used in Neurological Disorder Treatment:
Benzyl piperidine-1-carboxylate has demonstrated potential in the treatment of neurological disorders. It is used as a therapeutic agent to address specific conditions, capitalizing on its chemical properties to modulate neurological functions and alleviate symptoms.
Used as a Precursor in Psychoactive Substance Production:
benzyl piperidine-1-carboxylate also serves as a precursor in the production of psychoactive substances. Its role in this application is crucial for the synthesis of compounds that can affect mood, consciousness, and perception, which are important in various therapeutic and research contexts.

Upstream product

• 110-89-4 piperidine 
• 501-53-1 benzyl chloroformate 
• 75819-24-8 3-benzyloxycarbonyl-2-oxazolone 
• 124-38-9 carbon dioxide 
• 100-44-7 benzyl chloride 
• 419533-86-1 benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 40807-61-2 4-hydroxy-4-phenylpiperidin 
• 100-42-5 styrene 
• 885275-00-3 4-iodo-piperidine-1-carboxylic acid benzyl ester 
• 166953-64-6 benzyl 4-bromo-1-piperidinecarboxylate 
• 201230-82-2 carbon monoxide 
• 100-51-6 benzyl alcohol 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 87905-98-4 5-<(benzyloxycarbonyl)amino>pentanol 

Downstream Products

• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 92599-77-4 benzyl 2,3-diacetoxy-1-piperidinecarboxylate 
• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 
• 711002-74-3 (RS)-benzyl 3-aminopiperidine-1-carboxylate 
• 885069-22-7 3-cyano-piperidine-1-carboxylic acid benzyl ester 
• 174621-92-2 benzyl 3-acetoxypiperidine-1-carboxyate 
• 1186400-96-3 Benzyl 4-(2-(4-methoxyphenylthio)ethylcarbamoyl)piperazine-1-carboxylate 
• 1010732-19-0 2,3,4-triacetoxy-piperidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

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.

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides

We describe the development of the first reductive cross-electrophile coupling between alkyl sulfones and aryl bromides. The use of alkyl sulfones offers strategic advantages over other alkyl electrophiles as they can be incorporated into molecules in unique ways and permit α-functionalization prior to coupling. The conditions developed here enable incorporation of a wide array of aromatic rings onto (fluoro)alkyl scaffolds with broad functional group tolerance and generality, making this a practical method for late-stage diversification.

A Simple, efficient, Catalyst-Free and Solvent-Less Microwave-Assisted process for N-Cbz Protection of Several amines

A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.

Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions

The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction involves the activation of the hydroxyl group via the use of orthoesters. Despite the reduced nucleophilicity of carbamate nitrogen, this reaction system provides several types of pyrrolidines and piperidines in good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.

Light-Mediated Reductive Debromination of Unactivated Alkyl and Aryl Bromides

Cleavage of carbon-halogen bonds via either single-electron reduction or atom transfer is a powerful transformation in the construction of complex molecules. In particular, mild, selective hydrodehalogenations provide an excellent follow-up to the application of halogen atoms as directing groups or the utilization of atom transfer radical addition (ATRA) chemistry for the production of hydrocarbons. Here we combine the mechanistic properties of photoredox catalysis and silane-mediated atom transfer chemistry to accomplish the hydrodebromination of carbon-bromide bonds. The resulting method is performed under visible light irradiation in an open vessel and is capable of the efficient reduction of a variety of unactivated alkyl and aryl substrates.

Cis-Trans Conformational Analysis of δ-Azaproline in Peptides

The cis-trans isomerization and conformer specificity of δ-azaproline and its carbamate-protected form in linear and cyclic peptides were investigated using NMR and α-chymotrypsin assay. Comparisons of the chemical shift value of the α-hydrogen in each case of δ-azaproline-containing peptides with conformer-specific locked diketopiperazines reveal the fact that an upfield chemical shift value corresponds to cis conformer and a downfield value corresponds to a trans conformer. δ-Azaproline adopts cis-conformation in simple amides, dipeptides, and tripeptides whereas its carbamate-protected form adopts trans-conformation. In the case of longer, linear or cyclic peptides, vice versa results are obtained. Interestingly, in all these peptides exclusively one conformer, either cis or trans, is stabilized. This cis-trans isomerization is independent of both temperature and solvents; only the δ-nitrogen protecting group plays key role in the isomerization. δ-Azaproline is conformer-specific in either of its protected or deprotected forms, which is a unique property of this proline. Unlike other covalently modified proline surrogates, this isomerization of δ-azaproline can be tuned easily by a protecting group. The mechanism of cis-trans isomerization of δ-azaproline during deprotection and reprotection is supported by theoretical calculations.

Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight

A direct, catalytic hydrodecarboxylation of primary, secondary, and tertiary carboxylic acids is reported. The catalytic system consists of a Fukuzumi acridinium photooxidant with phenyldisulfide acting as a redox-active cocatalyst. Substoichiometric quantities of Hünigs base are used to reveal the carboxylate. Use of trifluoroethanol as a solvent allowed for significant improvements in substrate compatibilities, as the method reported is not limited to carboxylic acids bearing α heteroatoms or phenyl substitution. This method has been applied to the direct double decarboxylation of malonic acid derivatives, which allows for the convenient use of dimethyl malonate as a methylene synthon. Kinetic analysis of the reaction is presented showing a lack of a kinetic isotope effect when generating deuterothiophenol in situ as a hydrogen atom donor. Further kinetic analysis demonstrated first-order kinetics with respect to the carboxylate, while the reaction is zero-order in acridinium catalyst, consistent with another finding suggesting the reaction is light limiting and carboxylate oxidation is likely turnover limiting. Stern-Volmer analysis was carried out in order to determine the efficiency for the carboxylates to quench the acridinium excited state.

N-Urethane protection of amines and amino acids in an ionic liquid

An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.