349446-97-5

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 349446-96-4 {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine 
• 459-32-5 4-fluorocinnamic acid 
• 3449-63-6 3-(4-fluorophenyl)pentan-1,5-dioic acid 
• 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 
• 349446-91-9 (3S,1'S)-3-(4-fluorophenyl)-5-oxo-5-(1'-phenylethylamino)pentanoic acid 
• 1381968-84-8 C₂₀H₃₁NO₃Si 
• 352-13-6 4-flourophenylmagnesium bromide 
• 349446-94-2 (4R,1'S)-4-(4-fluorophenyl)-1-(1'-phenylethyl)piperidin-2-one 
• 349446-90-8 2-(4-fluorophenyl)-1,1,3-trimethoxy carbonyl propane 
• 349446-95-3 (3S,4R,1'S)-4-(4-fluorophenyl)-3-methoxycarbonyl-1-(1'-phenylethyl)piperidin-2-one 
• 100891-10-9 methyl p-fluorocinnamate 
• 4926-12-9 4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione 

Relevant academic research and scientific papers

Diastereoconvergent Synthesis of (–)-Paroxetine

A diastereoconvergent approach to (–)-paroxetine from diastereomeric 3,4-epoxy-2-piperidones is reported. For this synthesis, a regioselective and stereodivergent CuI-catalyzed epoxide-ring-opening reaction of epoxyamide precursors to give the 4-(4-fluorophenyl)-2-piperidone skeleton with the correct absolute configuration is crucial. Using CuBr·SMe2 as a catalyst, the epoxide-ring-opening reaction takes place with inversion of configuration; the configuration is retained when CuI is used.

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.