298690-89-8

Basic information

• Product Name: (R)-2-(4-Fluorophenyl)pyrrolidine
• Synonyms: (R)-2-(4-Fluorophenyl)pyrrolidine;(2R)-2-(4-fluorophenyl)pyrrolidine;(R)-2-(4-FLUOROPHENYL)PYRROLIDINE-HCL
• CAS NO: 298690-89-8
• Molecular Formula: C₁₀H₁₂FN
• Molecular Weight: 165.21
• Product Categories: API intermediates
• Mol File: 298690-89-8.mol

Chemical Properties

• Boiling Point: 235.5 °C at 760 mmHg
• Flash Point: 96.3 °C
• Appearance: /
• Density: 1.078 g/cm³
• Vapor Pressure: 0.0497mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.76±0.10(Predicted)
• CAS DataBase Reference: (R)-2-(4-Fluorophenyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(4-Fluorophenyl)pyrrolidine(298690-89-8)
• EPA Substance Registry System: (R)-2-(4-Fluorophenyl)pyrrolidine(298690-89-8)

Safety Data

• Hazardous Substances Data: 298690-89-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-2-(4-Fluorophenyl)pyrrolidine is used as a potential drug target for the development of treatments for various neurological and psychiatric conditions. Its unique structure and chiral properties offer opportunities for the design of novel therapeutic agents that can modulate specific biological pathways implicated in these disorders.
Used in Medicinal Chemistry:
(R)-2-(4-Fluorophenyl)pyrrolidine serves as a valuable compound in medicinal chemistry for the synthesis of new drug candidates. Its structural features can be further modified to enhance its pharmacological properties, such as potency, selectivity, and bioavailability, making it a promising starting point for the development of innovative medications.
Used in Drug Discovery:
In the field of drug discovery, (R)-2-(4-Fluorophenyl)pyrrolidine is utilized as a lead compound for the identification of new therapeutic agents. Its chiral nature allows for the exploration of the different biological activities of its enantiomers, potentially leading to the discovery of more effective and safer drugs.
Further research is required to fully understand the potential uses and implications of (R)-2-(4-Fluorophenyl)pyrrolidine in these fields, as well as to optimize its properties for specific applications.

InChI:InChI=1/C10H12FN/c11-9-5-3-8(4-6-9)10-2-1-7-12-10/h3-6,10,12H,1-2,7H2/t10-/m1/s1

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 22217-86-3 2-(4-fluorophenyl)-Δ¹-pyrrolidine 
• 1765-93-1 4-fluoroboronic acid 
• 298690-60-5 (R)-2-(4-fluorophenyl)-1-tosylpyrrolidine 

Downstream Products

• 885044-22-4 (R)-tert-butyl 2-(4-fluorophenyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

Tackling N-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of α-Chiral Amines

A readily activated iron alkyl precatalyst effectively catalyzes the highly enantioselective hydroboration of N-alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N-alkyl imines provided the corresponding α-chiral amines in excellent yields and with up to >99 % ee. The applicability of this base metal catalytic system was further demonstrated with the synthesis of the pharmaceuticals Fendiline and Tecalcet.

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.

Enantioselective Direct Synthesis of Free Cyclic Amines via Intramolecular Reductive Amination

Chiral cyclic amines can be prepared via intramolecular reductive amination of N-Boc-protected amino ketones in a one-pot process. With the complex of iridium and f-spiroPhos as the catalyst, a range of N-Boc-protected amino ketones are smoothly transformed into chiral cyclic free amines in high yields and excellent enantioselectivities (up to 97% ee). Moreover, this method can also be successfully applied to the synthesis of a κ-opioid receptor selective antagonist, (S)-1.

An (R)-imine reductase biocatalyst for the asymmetric reduction of cyclic imines

Although the range of biocatalysts available for the synthesis of enantiomerically pure chiral amines continues to expand, few existing methods provide access to secondary amines. To address this shortcoming, we have over-expressed the gene for an (R)-imine reductase [(R)-IRED] from Streptomyces sp. GF3587 in Escherichia coli to create a recombinant whole-cell biocatalyst for the asymmetric reduction of prochiral imines. The (R)-IRED was screened against a panel of cyclic imines and two iminium ions and was shown to possess high catalytic activity and enantioselectivity. Preparative-scale synthesis of the alkaloid (R)-coniine (90 % yield; 99 % ee) from the imine precursor was performed on a gram-scale. A homology model of the enzyme active site, based on the structure of a closely related (R)-IRED from Streptomyces kanamyceticus, was constructed and used to identify potential amino acids as targets for

Asymmetric reduction of cyclic imines catalyzed by a whole-cell biocatalyst containing an (S)-imine reductase

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Highly enantioselective arylation of N -tosylalkylaldimines catalyzed by rhodium-diene complexes

A highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines has been developed. The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions is the key to achieving high yield and enantioselectivity. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure. Furthermore, excellent results are also obtained for the imine substrates with the more readily cleavable N-nosyl protecting group.