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 is known for its nootropic and memory-enhancing activities in rats and has demonstrated prognostic value in cancer patients. (R)-2-Phenylpyrrolidine has the ability to inhibit the growth of human cancer cells and exhibits high affinity for binding to tropomyosin and growth factors. However, it does not have any known effects on kinase activities, amines, factor receptors, or synthetic activity.

Uses

Used in Pharmaceutical Industry:
(R)-2-Phenylpyrrolidine is used as a pharmaceutical agent for its memory-enhancing and nootropic properties, potentially benefiting patients with cognitive impairments or those seeking cognitive enhancement.
Used in Cancer Treatment:
(R)-2-Phenylpyrrolidine is used as an anticancer agent for its ability to inhibit the growth of human cancer cells. It has shown prognostic value in cancer patients and may be employed in the development of novel cancer treatments.
Used in Drug Design and Development:
Due to its high affinity for binding to tropomyosin and growth factors, (R)-2-Phenylpyrrolidine can be used as a starting point for the design and development of new drugs targeting these proteins, which may have applications in various therapeutic areas, including cancer treatment and other diseases involving these targets.

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 
• 154777-15-8 (2R,5S,8R)-2,8-diphenyl-1-aza-4-oxabicyclo<3.3.0>octane 
• 167642-29-7 (R)-N-trityl 2-phenylpyrrolidine 
• 860640-21-7 (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine 
• 860640-13-7 2-Methyl-propane-2-sulfinic acid ((R)-3-[1,3]dioxan-2-yl-1-phenyl-propyl)-amide 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 445433-35-2 pinanediol 4-azido-1-phenylbutylboronate 
• 445433-30-7 [2(1R),4R,5R]-4,5-dicyclohexyl-2-[4-azido-2-[(1-phenyl)butyl]]-1,3,2-dioxaborolane 
• 167642-27-5 (S)-(-)-4-amino-1-phenyl-1-butanol 
• 167642-28-6 (S)-1-Phenyl-4-(trityl-amino)-butan-1-ol 
• 167642-19-5 (S)-(-)-4-nitro-1-phenyl-1-butanol 
• 100-52-7 benzaldehyde 
• 153924-63-1 β-[(phenylmethylene)amino]-[R-(E)-]-benzeneethanol 
• 154777-12-5 (4R-1'R)-4-(2'-hydroxy-1'-phenylethylamino)-4-phenylbutanal dimethyl acetal 

Downstream Products

• 91539-41-2 (R)-N-benzoyl-2-phenylpyrrolidine 
• 860640-20-6 (R)-1-((R)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine 
• 860640-21-7 (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine 
• 700-91-4 2-phenyl-1-pyrroline 
• 123409-81-4 10bR-1,2,3,5,6,10bβ-hexahydro-6-phenylpyrrolo<2,1-a>isoquinoline 
• 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 
• 1210854-81-1 C₂₅H₂₂F₄N₂O 
• 1210854-82-2 C₂₅H₂₂F₄N₂O 

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.