6913-92-4

Usage

Uses

1-Benzyl-3-pyrroline was used in synthesis of (S)-1-benzyl-3-hydroxypyrrolidine.

InChI:InChI=1/C11H13N/c1-2-6-11(7-3-1)10-12-8-4-5-9-12/h1-7H,8-10H2

Upstream product

• 109-96-6 3-Pyrroline 
• 109-97-7 pyrrole 
• 98-88-4 benzoyl chloride 
• 1476-11-5 Z-1,4-dichlorobutene 
• 100-46-9 benzylamine 
• 1953-56-6 (Z)-but-2-ene-1,4-diyl dimethanesulfonate 
• 100-39-0 benzyl bromide 
• 1197-51-9 N-propargylbenzylamine 
• 50-00-0 formaldehyd 
• 100-44-7 benzyl chloride 
• 31410-11-4 N-benzyl-N-(but-2-en-1-yl)but-2-en-1-amine 
• 4383-26-0 N,N-di-2-propenylbenzylamine 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 124-38-9 carbon dioxide 

Downstream Products

• 2051-97-0 1-benzyl-1H-pyrrole 
• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 775-15-5 1-benzyl-3-pyrrolidinol 
• 162108-77-2 N-Benzyl-Δ³-pyrrolin-N-oxid 
• 75390-09-9 3-benzyl-6-oxa-3-azabicyclo[3.1.0]-hexane 
• 29897-82-3 N-benzylpyrrolidine 
• 1028289-32-8 benzyl-(2-sec-butyl-but-3-enyl)-amine 
• 479090-72-7 5-benzyl-3-(tetrahydropyran-2-yloxymethyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole 
• 954416-87-6 2-benzyl-5-phenyl-1,2,3,3a-tetrahydrocyclopenta[c]pyrrol-4(6aH)-one 
• 31970-04-4 1-carboxybenzyl-3-pyrrolidine 

Relevant academic research and scientific papers

Vanadium Imido NHC Complexes for Ring-Closing Olefin Metathesis Reactions

Vanadium bis-phosphine imido and oxo chloride alkylidenes have been extensively applied in the ring-closing metathesis of various acyclic olefins. However, their reactions involving ethylene have shown limited productivity due to rapid decomposition. The

Preparation method of medical intermediate N-BOC-3-pyrroline

The invention discloses a preparation method of a medical intermediate N-BOC-3-pyrroline. The method comprises the following steps: adding a proper amount of benzylamine, 3-bromopropylene, dichloromethane and an alkaline reagent into a reaction bottle for reaction to obtain an enamine compound; dissolving the enamine compound in dichloromethane, adding a catalyst (Grubbs first generation) for reaction, adding anhydrous sodium sulfate after adding water for layering, and performing suction filtration to obtain mother liquor; adding 1-chloroethyl chloroformate and methanol into the mother liquor, debenzylating to obtain pink solid, adding petroleum ether into the pink solid, pulping, and carrying out suction filtration to obtain 3-pyrroline hydrochloride; and re-dissolving the 3-pyrroline hydrochloride with water, adding an alkaline solution of NaHCO3 and (BOC)2O, stirring and reacting, extracting after the reaction is finished, separating out an organic phase, and drying to obtain a finished product of N-BOC-3-pyrroline. The method is low in raw material cost, simple in process step, high in yield, small in pollution, high in product purity and suitable for industrial production.

Preparation method of medical intermediate N-benzyl-3-pyrroline

The invention discloses a preparation method of a medical intermediate N-benzyl-3-pyrroline. The method comprises the following steps: adding a proper amount of benzylamine, maleic anhydride and a reaction medium into a reaction flask, and stirring for reaction to obtain a diamide compound; and dissolving a diamide compound in tetrahydrofuran, dropwise adding a proper amount of 70% red aluminum solution, and reducing the diamide compound to obtain N-benzyl-3-pyrroline; The method is low in raw material cost, simple in process step, high in yield, small in pollution, high in product purity and suitable for industrial production.

Ring-Closing Olefin Metathesis Catalyzed by Well-Defined Vanadium Alkylidene Complexes

Vanadium-based catalysts have shown activity and selectivity in ring-opening metathesis polymerization of strained cyclic olefins comparable to those of Ru, Mo, and W catalysts. However, the application of V alkylidenes in routine organic synthesis is limited. Here, we present the first example of ring-closing olefin metathesis catalyzed by well-defined V chloride alkylidene phosphine complexes. The developed catalysts exhibit tolerance to various functional groups, such as an ether, an ester, a tertiary amide, a tertiary amine, and a sulfonamide. The size and electron-donating properties of the imido group and the phosphine play a crucial role in the stability of active intermediates. Reactions with ethylene and olefins suggest that both β-hydride elimination of the metallacyclobutene and bimolecular decomposition are responsible for catalyst degradation.

Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions

The molybdenum benzylidynes [ArCMo(OC(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)C6H4 (2b), p-(CF3)C6H4 (2c), p-(NO2)C6H4 (2d), or 4-(NO2)-3-(CF3)C6H3 (2e), and [p-(NO2)C6H4CMo(OC(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylamide (3) to produce 1-tosyl-2,5-dihydro-1H-pyrrole (4) and ethylene. The scope of RCM catalytic activity of 2e, cross-metathesis of 1-hexene, and ring-opening metathesis polymerization of cyclooctene were explored. The X-ray crystal structure of 2e was determined. Variable-temperature 1H NMR spectra revealed the formation of intermediates during the reaction of 3 with 2f and the reforming of 2f after completion of the reaction. The use of 13C-labeled Mo benzylidyne did not show transfer of the carbon atom next to Mo to any of the products.

Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach

A zirconium catalyzed reductive cleavage of Csp3 and Csp2 carbon-heteroatom bonds is reported that makes use of a tethered alkene functionality as a traceless directing group. The reaction is successfully demonstrated on C-O, C-N, and C-S bonds and proposed to proceed via a hydrozirconation/β-heteroatom elimination sequence of an in situ formed zirconium hydride catalyst. The positional isomerization of the catalyst further enables the cleavage of homoallylic ethers and the removal of terminal allyl and propargyl groups.

Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts

Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppre

An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis

The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.

Practical synthetic process for enantiopure 1-benzyl-3-hydroxypyrrolidine

The synthesis of (S)-1-benzyl-3-hydroxypyrrolidine (S)-5 comprised the asymmetric hydroboration of 1-benzyl-3-pyrroline 4, followed by oxidation and chiral purification via diastereomeric salt formation. The asymmetric borane reagent was generated 'in situ' from NaBH4, BF3-OEt2, and (+)-α-pinene 1 (85% ee) and reacted with 4, prepared from cis-1,4-butenediol 3, to give crude product (S)-5. The following chiral purification via diastereomeric salt formation proceeded to afford (S)-5 with >99% ee. The optimized process was successfully scaled up to an industrial scale to produce a 252 kg batch of (S)-5.

Production process for bicyclic tetrahydropyrrole compounds

The present invention relates to a process using the Pauson-Khand Reaction to produce substituted bicyclic tetrahydropyrrole compounds of general formula (I),