392328-30-2

Upstream product

• 108-30-5 succinic acid anhydride 
• 108-55-4 glutaric anhydride, 
• 2033-24-1 cycl-isopropylidene malonate 
• 4480-83-5 1,4-dioxane-2,6-dione 
• 524012-93-9 (3S,4R)-3-[(3-carboxypropanoyl)oxymethyl]-4-(4'-fluorophenyl)-N-phenyloxycarbonylpiperidine 
• 392328-36-8 (3S,4R)-(-)-3-acetoxymethyl-4-(4'-fluorophenyl)-N-phenyloxycarbonylpiperidine 
• 1885-14-9 phenyl chloroformate 
• 188869-26-3 (3SR,4RS)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine 

Downstream Products

• 200572-33-4 (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester 
• 220548-73-2 (3S,4R)-(-)-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine hydrochloride 
• 125224-43-3 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine 

Relevant academic research and scientific papers

Optically pure paroxetine precursos

A biocatalytic process to obtain optically enriched precursors of trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidines,based on the enzymatic resolution of racemic derivatives of general formula III (where R3 is preferably phenyl or benzyl) using cyclic anhydrydes or the Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) as acylating agents of the hydroxyl group. Depending on the enzyme and the chosen reaction conditions, either of the two enantiomers may be obtained with high enantiomeric purity. These compounds are important intermediates in the synthesis of the paroxetine anti-depressive agent.

Anhydrides as acylating agents in the enzymatic resolution of an intermediate of (-)-Paroxetine

A new chemoenzymatic method for the preparation of an intermediate of (-)-Paroxetine is reported. Cyclic anhydrides are used as acylating agents in the lipase-catalyzed esterification of trans-4-(4′-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine in organic solvents. The best enantioselectivities are obtained with two different lipases from Candida antarctica. These two lipases show opposite stereochemical preference in these processes, so that both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer is an intermediate for the synthesis of (-)-Paroxetine.

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.