72216-06-9

Usage

Uses

Used in Organic Chemistry Research:
2-(4-Fluorophenyl)-pyrrolidine is used as a research compound for studying its chemical properties and potential applications in the field of organic chemistry.
Used in Drug Development:
2-(4-Fluorophenyl)-pyrrolidine is used as a building block in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs.
Used in Pharmaceutical Compound Synthesis:
2-(4-Fluorophenyl)-pyrrolidine is used as a key intermediate in the production of other organic chemicals, particularly in the synthesis of pharmaceutical compounds.
Used in Medicinal Chemistry Studies:
2-(4-Fluorophenyl)-pyrrolidine is used as a target for studies in medicinal chemistry, exploring its potential biological activities and applications in drug discovery.

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

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 22217-86-3 2-(4-fluorophenyl)-Δ¹-pyrrolidine 
• 456-22-4 4-Fluorobenzoic acid 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 123-75-1 pyrrolidine 
• 1493-23-8 (4-fluorophenyl)lithium 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 871724-26-4 C₂₃H₂₇FN₂O₄S 
• 1185502-90-2 C₂₈H₃₀F₄N₄O 
• 1219624-68-6 1-{2-[2-(4-fluorophenyl)pyrrolidin-1-yl]-2-oxoethyl}-3,3-diphenylpiperidin-2-one 
• 1169687-45-9 C₂₀H₁₈FN₇ 
• 1219832-95-7 1-[[7-(3,4-Dichloro-phenyl)-4,7-dihydro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]carbonyl]-2-(4-fluoro-phenyl)pyrrolidine 
• 1208147-41-4 C₂₈H₂₁Cl₂FN₄O 
• 298690-64-9 (RS)-4-{4-[2-(4-Fluoro-phenyl)-pyrrolidine-1-sulfonyl]-benzyl }-morpholine fumarate 

Relevant academic research and scientific papers

Stereocomplementary Synthesis of Pharmaceutically Relevant Chiral 2-Aryl-Substituted Pyrrolidines Using Imine Reductases

Exploring a collection of naturally occurring imine reductases (IREDs) identified two stereocomplementary IREDs with reducing activity toward sterically hindered 2-aryl-substituted pyrrolines. Using (R)-selective ScIR and (S)-selective SvIR, various chiral 2-aryl-substituted pyrrolidines with excellent enantioselectivity (>99% ee) were stereocomplementarily synthesized in good yield (60-80%), demonstrating the feasibility of IREDs for generating pharmaceutically relevant chiral 2-aryl-substituted pyrrolidine intermediates.

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.

Palladium-catalyzed ortho-olefination of 2-arylpyrrolidines: A tool for increasing structural complexity in nitrogen heterocycles

The dual role of the (2-pyridyl)sulfonyl unit as directing functionality and readily removable N-protecting group has enabled an efficient and practical transformation of 2-arylpyrrolidine derivatives into more complex tricyclic frameworks via palladium-catalyzed ortho-olefination with electron deficient alkenes and subsequent cyclization upon N-deprotection under mild conditions. The key cross coupling step in the presence of N-fluoro-2,4,6-trimethylpyridinium triflate ([F+]) as the terminal oxidant is both highly efficient and tolerant to a variety of steric and electronic changes at both coupling partners. By adequate choice of reductive conditions, the N-sulfonyl deprotection can be directed to the selective formation of benzo-fused pyrrolizidine or fused pyrrolidino-benzazapine frameworks.

Direct α-C-H bond functionalization of unprotected cyclic amines

Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.

Design, synthesis and biological evaluation of aminobenzyloxyarylamide derivatives as selective κ opioid receptor antagonists

Opioid receptors play an important role in both behavioral and mood functions. Based on the structural modification of LY2456302, a series of aminobenzyloxyarylamide derivatives were designed and synthesized as κ opioid receptor antagonists. The κ opioid receptor binding ability of these compounds were evaluated with opioid receptors binding assays. Compounds 1a-d showed high affinity for κ opioid receptor. Especially for compound 1c, exhibited a significant Kivalue of 15.7?nM for κ opioid receptor binding and a higher selectivity over μ and δ opioid receptors compared to (±)LY2456302. In addition, compound 1c also showed potent κ antagonist activity with κ IC50?=?9.32?nM in [35S]GTP-γ-S functional assay. The potential use of the representative compounds as antidepressants was also investigated. The most potent compound 1c not only exhibited potent antidepressant activity in the mice forced swimming test, but also displayed the effect of anti-anxiety in the elevated plus-maze test.

Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers

Design and synthesis of pyrazolodihydropyrimidines as KV1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development.

Hammett correlation of nornicotine analogues in the aqueous aldol reaction: Implications for green organocatalysis

(Chemical Equation Presented) A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with ρ = 1.14 (R2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organocatalyst.