188869-26-3

Basic information

• Product Name: TRANS-4-(4-FLUOROPHENYL)-3-PIPERIDINEME&
• Synonyms: TRANS-4-(4-FLUOROPHENYL)-3-PIPERIDINEME&;3-Piperidinemethanol, 4-(4-fluorophenyl)-, (3R,4S)-rel-;trans-4-(4-Fluorophenyl)-3-(hydroxymethyl)piperidine, [trans-4-(4-Fluorophenyl)piperidin-3-yl]carbinol
• CAS NO: 188869-26-3
• Molecular Formula: C12H16FNO
• Molecular Weight: 209.262
• Mol File: 188869-26-3.mol

Chemical Properties

• Boiling Point: 327.2°Cat760mmHg
• Flash Point: 151.7°C
• Appearance: /
• Density: 1.104g/cm³
• Vapor Pressure: 8.33E-05mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: TRANS-4-(4-FLUOROPHENYL)-3-PIPERIDINEME&(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-(4-FLUOROPHENYL)-3-PIPERIDINEME&(188869-26-3)
• EPA Substance Registry System: TRANS-4-(4-FLUOROPHENYL)-3-PIPERIDINEME&(188869-26-3)

Safety Data

• Hazardous Substances Data: 188869-26-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16FNO/c13-11-3-1-9(2-4-11)12-5-6-14-7-10(12)8-15/h1-4,10,12,14-15H,5-8H2/t10-,12?/m0/s1

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

• 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 
• 153888-27-8 ((3S,4R)-1-ethyl-4-(4-fluorophenyl)piperidin-3-yl)methanol 

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

A new route to 3,4-disubstituted piperidines: Formal synthesis of (-)-paroxetine and (+)-femoxetine

A new route to 3,4-disubstituted piperidines was developed using chiral 1,4-dihydropyridines as key intermediates, the synthetic utility of which was demonstrated by formal synthesis of (-)-paroxetine and (+)-femoxetine.

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.

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

Enantioselective Michael additions to α,β-unsaturated imides catalyzed by a salen-al complex

(Salen)aluminum complex 1b is an efficient catalyst for the conjugate addition of di- and trisubstituted nitriles to a wide range of acyclic alkyl- and aryl-substituted α,β-unsaturated imides. This new methodology provides access to multifunctional compounds that previously have not been readily accessible in enantioenriched form. Synthetic applications of these products include the preparation of enantiomerically enriched piperidines, as exemplified by an expedient asymmetric catalytic synthesis of (-)-paroxetine. Copyright

Novel process

Compounds of structure (1) are obtained by reduction of compounds of the structures Compounds of structure (1), especially where Z is a hydrogen atom or a 3,4-methylenedioxyphenyl group, are important intermediates for inter alia paroxetine.

Process for the preparation of 3-substituted 4-phenyl-piperidine derivative

Described herein is the process for the preparation of 3-substituted 4-phenyl-piperidine derivatives of formula (I) in which X is selected from H and F, and R is selected from the group consisting of H, C1-C6 alkyl, C3-C6 alkenyl, and benzyl, comprising three steps starting from the monoamide of malonic acid and cinnamic aldehyde, or derivatives thereof.

Novel process

A process for the preparation of a 4-aryl-3-oxymethyl-piperidine of structure (1) in which R is hydrogen or an alkyl, arylalkyl, allyl, acyl, carbonyloxyalkyl, carbonyloxyaryl, or carbonyloxyalkylaryl group, and Y is a hydrogen atom or an optionally substituted alkyl, arylalkyl, or aryl group, from a carboxy derivative of structure (2) where A is oxygen or sulphar, X is one or more of hydrogen, or a readily reducible group, Z represents either a hydrogen atom or an OY′ group in which Y′ is independently selected from the same groups as Y, and the broken line circle indicates bonding, appropriate to a tetrahydropyridine, dihydropyridine, pyridine, or piperidine ring said process comprising (a) when Y is a hydrogen atom, reducing the compound of structure (2), or (b) when Y is other than a hydrogen atom (i) forming an ether from the alcohol product of step (a), (ii) etherifying the aldehyde compound of structure (2) in which Z is hydrogen, or (iii) reducing the ester compound of structure (2) in which Z is OY′.

Enzymatic resolution of trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines, key intermediates in the synthesis of (-)-Paroxetine

Two Candida antarctica lipases catalyze the enantioselective acylation of N-substituted trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines in organic solvents. These two lipases show opposite stereochemical preference in these processes. Both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer, is an intermediate for the synthesis of (-)-Paroxetine.

Process for preparing arylpiperidine carbinol intermediates and derivatives

A process for the synthesis of arylpiperidine carbinol intermediates and derivatives is disclosed. A preferred process embodiment provides the synthesis of intermediate compounds of structural formula (I) and structural formula (II): where X is halo, C1-C10 alkoxy, C1-C10 haloalkyl, or hydroxy; R2 and R3 are each C1-C4 alkyl, and R2 and R3 are the same. The compound of structural formula (I) is made by condensing a corresponding cinnamonitrile with a corresponding diester malonate. The compound of structural formula (II) in the (±)-trans configuration is obtained by hydrogenating the compound of structural formula (I). The compounds of structural formula (I) and structural formula (II) are useful chemical intermediates for synthesizing 4-arylpiperidine-3-carbinols and their derivatives in (?)-trans configuration.