349446-91-9

Upstream product

• 459-32-5 4-fluorocinnamic acid 
• 1407597-91-4 (1S,3'S,4S)-5,5-di(2-methoxy-5-methylphenyl)-3-[3-(4-fluorophenyl)-4-(1-phenylethylcarbamoyl-1-oxobutyl)]-4-isopropyloxazolidin-2-one 
• 349446-90-8 2-(4-fluorophenyl)-1,1,3-trimethoxy carbonyl propane 
• 100891-10-9 methyl p-fluorocinnamate 
• 3449-63-6 3-(4-fluorophenyl)pentan-1,5-dioic acid 
• 4926-12-9 4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 349446-94-2 (4R,1'S)-4-(4-fluorophenyl)-1-(1'-phenylethyl)piperidin-2-one 
• 349446-96-4 {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine 
• 349446-92-0 (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide 
• 349446-93-1 (3S)-5-bromo-3-(4-fluorophenyl)pentanoic acid (1S)-1-phenylethylamide 
• 349446-95-3 (3S,4R,1'S)-4-(4-fluorophenyl)-3-methoxycarbonyl-1-(1'-phenylethyl)piperidin-2-one 
• 349446-97-5 Methanesulfonic acid (3S,4R)-4-(4-fluoro-phenyl)-1-((S)-1-phenyl-ethyl)-piperidin-3-ylmethyl ester 

Relevant academic research and scientific papers

An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one

The asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride 9 with lithiated chiral oxazolidin-2-one 8 has been studied. The desymmetrized product was formed with >90% de and converted into known intermediates for both (+)- and (-)-paroxetines.

Asymmetric syntheses of trans-3,4-disubstituted 2-piperidinones and piperidines

A convenient and practical method for the preparation of chiral 4-aryl-2-piperidinone from 3-arylglutaric anhydride and (S)-methylbenzylamine is described. Acylation or alkylation at the α-carbon of the chiral 4-aryl-2-piperidinone product afforded chiral trans-3,4-disubstituted 2-piperidinone derivatives and reduction of the chiral 2-piperidinones with lithium aluminum hydride provided the corresponding enantiomerically pure trans-3,4-disubstituted piperidines. This methodology has been successfully applied to the synthesis of the anti-depressant paroxetine.