200572-35-6

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, 1,1-dimethylethyl ester, (3S,4R)-
• CAS NO: 200572-35-6
• Molecular Formula: C24H28FNO5
• Molecular Weight: 429.488
• Mol File: 200572-35-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, 1,1-dimethylethyl ester, (3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, 1,1-dimethylethyl ester, (3S,4R)-(200572-35-6)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, 1,1-dimethylethyl ester, (3S,4R)-(200572-35-6)

Safety Data

• Hazardous Substances Data: 200572-35-6(Hazardous Substances Data)

Upstream product

• 533-31-3 Sesamol 
• 200572-34-5 (3S,4R)-tert-butyl 4-(4-fluorophenyl)-3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate 
• 16387-85-2 benzo[d][1,3]dioxol-5-yl 4-methylbenzenesulfonate 
• 200572-33-4 (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester 
• 347-93-3 3-chloro-4'-fluoropropiophenone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 37155-08-1 1-(4-fluorophenyl)-3-(4-methoxyphenylamino)propan-1-one 
• 125224-43-3 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine 
• 607375-32-6 4-(4-fluorophenyl)-1-(4-methoxyphenyl)-5,6-dihydro-1H-pyridin-2-one 
• 607375-33-7 (4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-piperidin-2-one 
• 607375-35-9 [(3S,4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-piperidin-3-yl]methanol 
• 607375-34-8 (3S,4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-oxopiperidin-3-carboxylic acid methyl ester 
• 1027570-33-7 N-[3-(4-fluoro-phenyl)-3-oxo-propyl]-N-(4-methoxy-phenyl)-malonamic acid ethyl ester 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 61869-08-7 paroxetine 
• 61869-08-7 paroxetine 
• 110429-35-1 (-)-paroxetine hydrochloride 
• 115-11-7 isobutene 

Relevant articles and documents

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.

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.

Synthesis of Enantiopure trans-3,4-Disubstituted Piperidines. An Enantiodivergent Synthesis of (+)- And (-)-Paroxetine

Reaction of (R)-phenylglycinol with methyl 5-oxopentanoate gave either bicyclic lactam cis-1 (the kinetic product) or its isomer trans-1 (under equilibrating conditions) as the major products, which were converted to the corresponding (cis or trans) unsaturated lactams 4 and 5. On treatment with lithium alkyl (or aryl) cyanocuprates, these chiral building blocks undergo conjugate addition to give enantiopure trans-3,4-substituted 2-piperidone derivatives in high yield and stereoselectivity. The synthetic potential of this transformation is illustrated by the synthesis of (+)-femoxetine and the two enantiomers of the known antidepressant paroxetine.