{(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine

Base Information

• Chemical Name: {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine
• CAS No.: 349446-96-4
• Molecular Formula: C₂₀H₂₄FNO
• Molecular Weight: 313.415
• Mol file: 349446-96-4.mol

Synonyms:{(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine

Chemical Property of {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine

There total 21 articles about {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[(S)-1-phenylethyl]piperidin-2-one → {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine (349446-96-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Reflux;

DOI:10.1002/ejoc.201700658

Reference yield: 65.0%

(3S,4R,1'S)-4-(4-fluorophenyl)-3-methoxycarbonyl-1-(1'-phenylethyl)piperidin-2-one (349446-95-3) → {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine (349446-96-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 72h; Heating;

DOI:10.1016/S0957-4166(01)00069-6

Reference yield:

4-flourophenylmagnesium bromide (352-13-6) → {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine (349446-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(l) iodide / diethyl ether / 2 h / 20 °C

1.2: 5 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: dmap / chloroform / 0.17 h / 20 °C

3.2: 5 h

4.1: 1,1'-azobis(1-cyanocyclohexanenitrile); tri-n-butyl-tin hydride / toluene / 0.67 h / Reflux

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux

With dmap; copper(l) iodide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; diethyl ether; chloroform; toluene;

DOI:10.1002/ejoc.201700658

upstream raw materials:

(3S,4R,1'S)-4-(4-fluorophenyl)-3-methoxycarbonyl-1-(1'-phenylethyl)piperidin-2-one

4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione

4-fluorocinnamic acid

3-(4-fluorophenyl)pentan-1,5-dioic acid

Downstream raw materials:

(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester

(3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine

paroxetine

(-)-paroxetine hydrochloride