201855-60-9

Basic information

• Product Name: trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol
• Synonyms: (-)-(3S,4R)-4-(4-Fluorophenyl)-1-(phenylmethyl)-3-piperidinemethanol;(-)-trans-1-Benzyl-4-(4-fluorophenyl)-3-hydroxymethylpiperidine;(3S,4R)-4-(4-Fluorophenyl)-1-(phenylmethyl)- 3-piperidinemethanol;trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol;Paroxetine Anhydrous EP Impurity H
• CAS NO: 201855-60-9
• Molecular Formula: C₁₉H₂₂FNO
• Molecular Weight: 299.38
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 201855-60-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 402.1°C at 760 mmHg
• Flash Point: 197°C
• Appearance: /
• Density: 1.139g/cm³
• Vapor Pressure: 3.45E-07mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol(201855-60-9)
• EPA Substance Registry System: trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol(201855-60-9)

Safety Data

• Hazardous Substances Data: 201855-60-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Thick Oil

Uses

Paroxetine intermediate

InChI:InChI=1/C19H22FNO/c20-18-8-6-16(7-9-18)19-10-11-21(13-17(19)14-22)12-15-4-2-1-3-5-15/h1-9,17,19,22H,10-14H2/t17-,19-/m0/s1

Upstream product

• 15014-25-2 malonic acid dibenzyl ester 
• 24654-55-5 trans-4-fluorocinnamaldehyde 
• 100-46-9 benzylamine 
• 1032429-79-0 (R)-dimethyl 2-(1-(4-fluorophenyl)-2-formylethyl)malonate 
• 51791-26-5 3-(4-fluoro-phenyl)-propenal 
• 216690-18-5 (3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester 
• 323203-13-0 (3S,4R)-ethyl 1-benzyl-4-(4-fluorophenyl)-6-hydroxy-2-oxopiperidine-3-carboxylate 
• 369593-35-1 isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate 
• 369593-37-3 isobutyl (3S,4R,5S)-1-benzyl-4-(4-fluorophenyl)-5-(hydroxymethyl)pyrrolidine-3-carboxylate 
• 369593-36-2 isobutyl (3S,6S,7R,7aR)-7-(4-fluorophenyl)-3-phenyl-5-oxo-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate 
• 369593-38-4 isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate 
• 511283-91-3 1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione 
• 130387-74-5 4-fluorophenylmagnesium chloride 
• 1027908-81-1 tert-Butyl-[(2R,3R)-3-(4-fluoro-phenyl)-5-iodo-2-iodomethyl-pentyloxy]-dimethyl-silane 

Downstream Products

• 201855-71-2 Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester 
• 105813-14-7 (3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine 
• 61869-08-7 paroxetine 

Relevant articles and documents

Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis

The catalytic enantioselective synthesis of the chiral key intermediate of the antidepressant (-)-paroxetine is demonstrated as a continuous flow process on multi-gram scale. The critical step is a solvent-free organocatalytic conjugate addition followed

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin

Short and efficient enantioselective syntheses of (-)-paroxetine and (+)-laccarin are described based on the highly stereospecific cleavage of C(3)-substituted 1,3-cyclic sulfamidates. The Royal Society of Chemistry.