61586-46-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylpyrrolidine is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a fundamental component in the creation of a wide array of medicinal compounds, contributing to the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
In the realm of organic chemistry, 3-Phenylpyrrolidine serves as a valuable building block for the preparation of diverse organic compounds. Its reactivity and structural properties make it an essential precursor in the synthesis of complex organic molecules for research and commercial applications.
Used in Agricultural Industry:
3-Phenylpyrrolidine is also a pivotal intermediate in the production of certain pesticides. Its role in the synthesis of these agrochemicals is crucial for developing effective and targeted pest control solutions, thereby supporting agricultural productivity and crop protection.

Upstream product

• 123724-21-0 (2S,3R)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid 
• 71657-88-0 (4R)-4-phenyl-2-pyrrolidone 
• 145549-11-7 tert-butyl (R)-3-phenylpyrrolidine-1-carboxylate 
• 5153-67-3 nitrostyrene 
• 163982-20-5 (R)-(-)-(2,2-Diphenylcyclopentoxy)ethene 
• 591-51-5 phenyllithium 
• 145549-09-3 (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol 
• 145549-03-7 (3S,7R,7aR)-3,7-Diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 145549-01-5 (3S,6S,7R,7aR)-5-Oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 
• 185067-05-4 ethyl 2-carbethoxy-3-cyano-3-phenylpropionate 
• 5292-53-5 diethyl benzalmalonate 
• 67159-52-8 (3R*,4S*)-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid 
• 52450-32-5 Ethyl (E)-2-oxo-4-phenylpyrrolidine-3-carboxylate 
• 138782-42-0 (3R,4R)-N-<(1R)-2-Hydroxy-1-phenylethyl>-2-oxo-4-phenylpyrrolidine-3-carboxamide 

Downstream Products

• 70665-33-7 2-(3-Phenyl-pyrrolidin-1-yl)-pyridine 1-oxide 
• 91539-42-3 (R)-N-benzoyl-3-phenylpyrrolidine 
• 1201986-77-7 (2S,4R)-tert-butyl-4-phenyl-2-((R)-3-phenylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate 
• 165883-19-2 (+)-(R)-3-phenyl-N-(p-toluenesulfonyl)pyrrolidine 
• 750584-06-6 1-methyl-3R-phenyl-pyrrolidine 

Relevant academic research and scientific papers

Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position

With the assistance of hydrogen bonds, the first asymmetric hydrogenation of β-cyanocinnamic esters is developed, affording chiral β-cyano esters with excellent enantioselectivities (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral GABA-derivatives such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with a single H-bond donor performs better than that with double H-bond donors, which is a novel discovery in the metalorganocatalysis area.

Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines giving 3-arylpyrrolidines: Protonation as a key step

A hydroxorhodium complex coordinated with (R)-segphos was found to catalyze the hydroarylation of 3-pyrrolines with arylboroxines under neutral conditions to give 3-arylpyrrolidines with high enantioselectivity in high yields.

Catalytic asymmetric michael reactions of acetaldehyde

(Chemical Equation Presented) Acetaldehyde, now a big contender: A silyl prolinol derivative was found to catalyze the first Michael addition of acetaldehyde with both aromatic and aliphatic nitroolefins in excellent enantioselectivities (see scheme, TMS = trimethylsilyl). The utility of the reaction is illustrated in the synthesis of three current pharmaceuticals and in the synthesis of an enantiopure 3-monosubstituted pyrrolidine.

Process for the preparation of enantiomerically enriched cyclic beta-aryl or heteroaryl carbocyclic acids

The present invention relates to a process for the preparation of cis substituted cyclic β-aryl or heteroaryl carboxylic acid derivatives in high diastereo- and enantioselectivity by enantioselective hydrogenation in accordance with the following scheme w

Asymmetric nitroalkene [4 + 2] cycloadditions: Enantioselective synthesis of 3-substituted and 3,4-disubstituted pyrrolidines

2-Substituted 1-nitroalkenes undergo highly diastereoselective, Lewis-acid-promoted, [4 + 2] cycloaddition with chiral vinyl ethers derived from (R)-2,2-diphenylcyclopentanol and (1R,2S)-2-phenylcyclohexanol to afford cyclic nitronates in high yields. The resulting nitronates were reduced with hydrogen at 160 psi in the presence of platinum oxide to afford enantiomerically enriched pyrrolidines (both as the free base and N-protected derivatives) in good yields. A series of 3-substituted pyrrolidines (71-97% ee) were prepared, as well as (3S,4R)-4-methyl-3-phenyl-N-(p-tolylsulfonyl)pyrrolidine (92% ee) and (3S,4S)-3,4-diphenylpyrrolidine (99% ee). The chiral auxiliaries can be recovered in nearly quantitative yields after hydrogenation.

The Synthesis of Aracemic 4-Substituted Pyrrolidinones and 3-Substituted Pyrrolidines. An Asymmetric Synthesis of (-)-Rolipram

Conjugate additions of RCuCNLi to the chiral α,β-unsaturated lactam 4 gives almost exclusive exo addition - a reversal in stereochemistry when cuprates were added to chiral lactam 1.The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage.The chemical yields as well as the enantiomeric purity were very high for this process.As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield.Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11.Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.

Resolution of 4-phenyl-2-pyrrolidinone: A versatile synthetic intermediate

A resolution of 4-phenyl-2-pyrrolidinone is described. The resulting enantiomerically pure pyrrolidinones are exploited as precursor to 3-phenylpyrrolidines and 3-phenyl-γ-amino acids (4-amino-3-phenylbutanoic acid derivatives).