125224-43-3

Basic information

• Product Name: (3S,4R)-(-)-4-(4'-FLUOROPHENYL)3-HYDROXYMETHYL)-PIPERIDINE
• Synonyms: (3S,4R)-4-(4-Fluorophenyl)piperidine-3-methanol;N-Desmethyl Paroxol;3-Piperidinemethanol, 4-(4-fluorophenyl)-, (3S,4R)-;(3S,4R)-(-)-4-(4-Fluorophenyl)-3-piperidinemethanol;Paroxetine Anhydrous EP Impurity I;(3S,4R)-trans-(-)-4-(4-Fluorophenyl)-3-hydroxymethyl-piperidine
• CAS NO: 125224-43-3
• Molecular Formula: C₁₂H₁₆FNO
• Molecular Weight: 209.262
• EINECS: 212-273-5
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 125224-43-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 81-83 °C
• Boiling Point: 327.2 °C at 760 mmHg
• Flash Point: 151.7 °C
• Appearance: /
• Density: 1.104
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 14.93±0.10(Predicted)
• CAS DataBase Reference: (3S,4R)-(-)-4-(4'-FLUOROPHENYL)3-HYDROXYMETHYL)-PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-(-)-4-(4'-FLUOROPHENYL)3-HYDROXYMETHYL)-PIPERIDINE(125224-43-3)
• EPA Substance Registry System: (3S,4R)-(-)-4-(4'-FLUOROPHENYL)3-HYDROXYMETHYL)-PIPERIDINE(125224-43-3)

Safety Data

• Hazardous Substances Data: 125224-43-3(Hazardous Substances Data)

Usage

Uses

A metabolite of Paroxetine, also an intermediate for the production of the antidepressant

Upstream product

• 392328-28-8 (3S,4R)-(-)-N-allyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine 
• 392328-30-2 (3S,4R)-(-)-4-(4'-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine 
• 392328-26-6 (3S,4R)-(-)-N-benzyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine 
• 872544-47-3 (3S,4R)-4-(4-fluorophenyl)piperidine-3-carboxylic acid methyl ester 
• 607375-35-9 [(3S,4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-piperidin-3-yl]methanol 
• 947169-72-4 C₁₃H₁₄FNO₃ 
• 947169-69-9 C₁₄H₁₇FO₅ 
• 947169-71-3 C₁₄H₁₆FN₃O₄ 
• 947169-85-9 2-[(R)-1-(4-Fluoro-phenyl)-allyl]-malonic acid dimethyl ester 
• 872544-44-0 (S)-4-(4-Fluoro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 
• 872544-45-1 (S)-4-(4-Fluoro-phenyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 
• 872544-56-4 [(S)-1-Benzoyl-4-(4-fluoro-phenyl)-1,4-dihydro-pyridin-3-yl]-((S)-4-phenyl-2-thioxo-thiazolidin-3-yl)-methanone 
• 1493-23-8 (4-fluorophenyl)lithium 
• 230309-03-2 (4S)-(4-phenyl-2-thioxo-1,3-diazolidin-3-yl)-pyridin-3-yl-methanone 

Downstream Products

• 200572-33-4 (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester 
• 61869-08-7 paroxetine 
• 200572-35-6 (3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine 
• 110429-35-1 (-)-paroxetine hydrochloride 
• 200572-34-5 (3S,4R)-tert-butyl 4-(4-fluorophenyl)-3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate 
• 220548-73-2 (3S,4R)-(-)-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine hydrochloride 
• 1448710-25-5 tert-butyl (3S,4R)-3-[(1,3-dihydro-2-benzofuran-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate 
• 923932-19-8 (3S,4R)-4-(4-fluorophenyl)-3-formylpiperidine-1-carboxylic acid tert-butyl ester 
• 923932-21-2 (-)-(3S,4R)-4-(4-fluoro-phenyl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 872544-47-3 (3S,4R)-4-(4-fluorophenyl)piperidine-3-carboxylic acid methyl ester 

Relevant articles and documents

Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (-)-paroxetine

An Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxide is described. Asymmetric allylic alkylation of terminal allylic carbonates proceeded using 5 mol % of Ir catalyst, 5 mol % of DIAPHOX 1i, 10 mol % of NaPF6, 10 mo

Optically pure paroxetine precursors

A biocatalytic process to obtain optically enriched derivatives of trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidines, based on the enzymatic resolution of racemic precursors of formula III (where R3 is preferably phenyl or benzyl) by acylatio

Catalytic enantioselective conjugate reduction of lactones and lactams

A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of α,β-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl2·H2O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.