17416-73-8

Upstream product

• 591-12-8 5-methyl-2-furanone 
• 100-46-9 benzylamine 
• 123-76-2 levulinic acid 

Downstream Products

• 448957-53-7 N-benzyl-4-hydroxypentylamine 
• 22568-12-3 1-benzyl-5-methylene-pyrrolidin-2-one 
• 175787-35-6 4-Methoxyamino-pentanoic acid benzylamide 
• 175787-34-5 N-(3-Benzylcarbamoyl-1-methyl-propyl)-N-methoxy-4-nitro-benzamide 
• 91640-09-4 5-methyl-1-(phenylmethyl)-2-pyrrolidinone 
• 448957-42-4 5-[N-benzyl-(N-tert-butyloxycarbonyl)]amino-2-methyl-2-nitro-1-(diphenylphosphatoxy)-pentane 
• 448957-45-7 5-(N-benzylamino)-2-methyl-2-nitro-1-(diphenylphosphatoxy)-pentane 
• 448957-58-2 5-[N-benzyl-(N-tert-butyloxycarbonyl)]amino-2-methyl-2-nitro-1-pentanol 
• 448957-40-2 5-[N-benzyl-(N-tert-butyloxycarbonyl)]amino-2-nitropentane 
• 448957-38-8 5-[N-benzyl-(N-tert-butyloxycarbonyl)]amino-2-pentanol 
• 448957-55-9 5-[N-benzyl-(N-tert-butyloxycarbonyl)]amino-2-bromopentane 
• 6560-75-4 1-benzyl-3-methylpiperidine 

Relevant academic research and scientific papers

Amino-Acid-Catalyzed Direct Aldol Bioconjugation

A site-specific bioconjugation was developed based on direct aldol coupling using amino-acid-derived organocatalysts. The functionalization exhibits fast kinetics and occurs under mild, biocompatible conditions (viz., aqueous media, moderate temperature, and neutral pH). The resulting bioconjugates were found to be stable toward abundant aldolase enzymes, as well as acidic and basic pH. The methodology was demonstrated through conjugation of a variety of small molecules, dyes, and peptides to proteins, including a single-domain antibody, which was then used for cellular imaging.

Highly Stable Porous-Carbon-Coated Ni Catalysts for the Reductive Amination of Levulinic Acid via an Unconventional Pathway

The catalytic conversions of biomass and its derivatives into fuels and chemicals require active and stable catalysts. Non-noble-metal catalysts typically suffer from deactivation due to the leaching and sintering of the metal species in liquid-phase reactions. In this work, we report a facile synthesis of porous-carbon-coated Ni catalysts supported on carbon nanotubes (CNFx@Ni@CNTs) by atomic layer deposition for the reductive amination of levulinic acid (LA) with amines to pyrrolidones. Under the protection of porous carbon with a moderate thickness, the optimized CNF30@Ni@CNTs catalyst showed a 99% yield of pyrrolidones and recyclability of up to 20 runs without the leaching and sintering of Ni nanoparticles. On the basis of verification experiments and density functional theory calculations, we determined that our Ni-catalyzed reductive amination of LA with amines underwent an unconventional pathway via amides as the first intermediate, followed by tandem cyclization, intramolecular dehydration, and hydrogenation to the desired pyrrolidones. This pathway was completely different from the reported imine-intermediated route in Pt-catalyzed systems. This work provides insights into the design of active and stable heterogeneous catalysts for liquid-phase reactions as well as into switching reaction pathways to realize the replacement of noble metals for the transformation of biobased multifunctional substrates.

Palladium-catalyzed selective hydrogenolysis of N-alkyl(aryl)-substituted γ-keto amides as an approach to γ-lactams or linear amides

A palladium-catalyzed hydrogenolysis of N-substituted γ-keto amides can proceed with participation of tautomeric 5-hydroxypyrrolidin-2-ones and give either pyrrolidin-2-ones, or linear amides, or their mixtures, depending on the substrate structure.

Triflic anhydride mediated cyclization of 5-hydroxy-substituted pyrrolidinones for the preparation of α-trifluoromethylsulfonamido furans

The reaction of α-angelica lactone with alkylamines under aqueous conditions afforded 5-hydroxy-5-methylpyrrolidinones in high yield. When the reaction was carried out under anhydrous conditions, the only products obtained were the corresponding 4-oxopentanoic acid amides. Treatment of either class of compound with triflic anhydride (Tf2O) in pyridine resulted in the formation of various substituted sulfonamidofurans. The suggested mechanism involves initial formation of an iminium ion which is subsequently transformed into a transient imino triflate. Cyclization of the highly electrophilic imine onto the oxygen atom of the adjacent carbonyl group generates an imino dihydrofuran intermediate. This species reacts further with another equivalent of Tf2O to give the observed product. The nature of the Lewis acid used was found to affect the outcome of the cyclization reaction. In certain cases, the sulfonamide furan was utilized as a cycloaddition substrate for the synthesis of indolines and related heterocyclic systems.

Generation and trapping of alkene radical cations under nonoxidizing conditions: Formation of six-membered rings by exo- and endo-mode cyclizations

(Matrix presented) It is demonstrated that alkene radical cations generated by the radical ionic fragmentation of β-(phosphatoxy)alkyl radicals undergo efficient nucleophilic capture by amines in either the 6-exo or 6-endo modes, leading to six-membered n

Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support

Ketones and aldehydes were formed in low to good yields in reactions of Weinreb-type amides on solid support and no overaddition occurred.

SUBSTITUTION OF 3H-FURAN-2-ONES IN AMINATION AND HYDROAMINATION REACTIONS

The amination and hydroamination of 5-alkyl-3H-furan-2-ones and their 3-benzylidene- and 3-formyl-derivatives were studied.The characteristics of the reactions, the requirements for the nature of the nucleophilic reagents, and the reaction conditions leading to the destruction of the furan ring and recyclization to pyrrolidinone and pyrrolinone structures are indicated.