56523-47-8

Basic information

• Product Name: (R)-2-Phenylpyrrolidine
• Synonyms: (R)-2-Phenylpyrrolidine;(2R)-2-phenylpyrrolidine; 56523-47-8
• CAS NO: 56523-47-8
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• Product Categories: pharmaceutical intermediate;Chiral heterocyclic compounds
• Mol File: 56523-47-8.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 237 °C at 760 mmHg
• Flash Point: 98.3 °C
• Appearance: /
• Density: 0.988 g/cm³
• Vapor Pressure: 0.0459mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.13±0.10(Predicted)
• CAS DataBase Reference: (R)-2-Phenylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Phenylpyrrolidine(56523-47-8)
• EPA Substance Registry System: (R)-2-Phenylpyrrolidine(56523-47-8)

Safety Data

• Hazardous Substances Data: 56523-47-8(Hazardous Substances Data)

Usage

Description

(R)-2-Phenylpyrrolidine is a boronic ester that can be administered orally. It has been shown to have nootropic and memory-enhancing activities in rats, but it does not have any known effects on kinase activities, amines, factor receptors, or synthetic activity.

Uses

(R)-2-Phenylpyrrolidine has also been shown to have prognostic value in cancer patients and can inhibit the growth of human cancer cells. This drug has been shown to bind to tropomyosin and growth factors with high affinity.

InChI:InChI=1/C10H13N/c1-2-5-9(6-3-1)10-7-4-8-11-10/h1-3,5-6,10-11H,4,7-8H2/t10-/m1/s1

Upstream product

• 700-91-4 2-phenyl-1-pyrroline 
• 860640-13-7 2-Methyl-propane-2-sulfinic acid ((R)-3-[1,3]dioxan-2-yl-1-phenyl-propyl)-amide 
• 860640-20-6 (R)-1-((R)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine 
• 174311-02-5 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 313352-62-4 (R)-(+)-5-phenylpyrrolidin-2-one 
• 116437-41-3 tert-butyl (4-oxo-4-phenyl-butyl)-carbamate 
• 1207729-66-5 (S)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine 
• 56523-58-1 (-)-(S)-2-Phenylpyrrolidine hydrochloride 
• 56553-09-4 (S)-(-)-5-phenylpyrrolidin-2-one 
• 154777-15-8 (2R,5S,8R)-2,8-diphenyl-1-aza-4-oxabicyclo<3.3.0>octane 
• 2051-95-8 succinylbenzene 
• 882-33-7 diphenyldisulfane 
• 132959-49-0 (+)-N-<2-(2(R)-Phenyl-1-(phenylthio)ethyl)>-5(S)-phenyl-2-pyrrolidine 

Downstream Products

• 91539-41-2 (R)-N-benzoyl-2-phenylpyrrolidine 
• 938-36-3 (S)-(-)-1-methyl-2-phenylpyrrolidine 
• 1376191-20-6 C₂₇H₃₅N 
• 1179523-32-0 C₁₀H₁₁N 
• 1163793-61-0 4-[(S)-4-carboxy-2-({5-[2-oxo-2-((S)-2-phenyl-pyrrolidin-1-yl)-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester 
• 98421-41-1 2,2,2-Trifluoro-1-((S)-2-phenyl-pyrrolidin-1-yl)-ethanone 

Relevant articles and documents

Zinc-Catalyzed Asymmetric Hydrosilylation of Cyclic Imines: Synthesis of Chiral 2-Aryl-Substituted Pyrrolidines as Pharmaceutical Building Blocks

The first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex is reported. In situ generated zinc-ProPhenol complex with silane afforded pharmaceutically relevant enantioenriched 2-aryl-substituted pyrrolidines in high yields and with excellent enantioselectivities (up to 99% ee). The synthetic utility of presented methodology is demonstrated in an efficient synthesis of the corresponding chiral cyclic amines, being pharmaceutical drug precursors to the Aticaprant and Larotrectinib. (Figure presented.).

A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters

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Enantioselective Synthesis of 2-Substituted Pyrrolidines via Intramolecular Reductive Amination

Catalyzed by the complex generated in situ from iridium and the chiral ferrocene ligand, tert -butyl (4-oxo-4-arylbutyl)carbamate substrates were deprotected and then reductively cyclised to form 2-substituted arylpyrrolidines in a one-pot manner, in which the intramolecular reductive amination was the key step. A range of chiral 2-substituted arylpyrrolidines were synthesised in up to 98percent yield and 92percent ee.