62624-46-8

Usage

Uses

Used in Organic Synthesis:
(S)-3-phenylpyrrolidine is utilized as a chiral building block in organic synthesis, playing a crucial role in the creation of pharmaceuticals and other biologically active molecules. Its distinctive stereochemistry allows for the development of enantioselective reactions, which are essential for producing compounds with specific biological activities.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-3-phenylpyrrolidine serves as a key component in the synthesis of various drugs and pharmaceutical intermediates. Its ability to impart chirality to synthesized compounds is particularly valuable for designing drugs with targeted therapeutic effects and reduced side effects.
Used as a Catalyst in Asymmetric Synthesis:
(S)-3-phenylpyrrolidine has been studied for its potential use as a catalyst in asymmetric synthesis. As a catalyst, it can facilitate reactions with high enantioselectivity, enabling the production of enantiomerically pure compounds, which is critical in pharmaceutical development where the desired biological activity often resides in one enantiomer.
Used in the Preparation of Drug Intermediates:
(S)-3-phenylpyrrolidine is employed in the preparation of drug intermediates, which are essential precursors in the synthesis of final drug products. Its presence in these intermediates can influence the final drug's efficacy, safety, and pharmacokinetic properties, underscoring its importance in the pharmaceutical industry.

Upstream product

• 59349-74-5 (S)-N-benzyl-3-phenylpyrrolidine 
• 62624-45-7 (S)-4-phenyl-1-tosylpyrrolidin-2-one 
• 185067-05-4 ethyl 2-carbethoxy-3-cyano-3-phenylpropionate 
• 17480-07-8 2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 5848-57-7 4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]benzene-1-sulfonamide 
• 4335-60-8 (E)-cinnamylamine 
• 52450-32-5 Ethyl (E)-2-oxo-4-phenylpyrrolidine-3-carboxylate 
• 67159-52-8 (3R*,4S*)-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid 
• 5292-53-5 diethyl benzalmalonate 
• 5153-67-3 nitrostyrene 
• 163982-20-5 (R)-(-)-(2,2-Diphenylcyclopentoxy)ethene 
• 138812-85-8 (3S,4S)-N-<(1R)-2-Hydroxy-1-phenylethyl>-2-oxo-4-phenylpyrrolidine-3-carboxamide 

Downstream Products

• 59349-74-5 (S)-N-benzyl-3-phenylpyrrolidine 

Relevant academic research and scientific papers

Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of trans-1,2-Disubstituted Alkenes

The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility of our method. A creative route for the synthesis of vernakalant and Enablex was also developed.

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.

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).