277743-59-6

Basic information

• Product Name: (3R,8aS)-6-(benzyloxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• Synonyms: (3R,8aS)-6-(benzyloxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS NO: 277743-59-6
• Molecular Weight: 506.46
• Mol File: 277743-59-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,8aS)-6-(benzyloxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,8aS)-6-(benzyloxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine(277743-59-6)
• EPA Substance Registry System: (3R,8aS)-6-(benzyloxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine(277743-59-6)

Safety Data

• Hazardous Substances Data: 277743-59-6(Hazardous Substances Data)

Upstream product

• 6026-86-4 methyl 4-formylbutanoate 
• 14273-92-8 methyl 5-hydroxypentanoate 
• 152555-02-7 (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 

Downstream Products

• 182957-44-4 (1aS,2aS,5R,6aS)-6-Oxo-5-phenyl-tetrahydro-1,3-dioxa-5a-aza-cyclopropa[f]indene-6a-carboxylic acid benzyl ester 
• 179179-81-8 (3R,4S)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine 
• 277743-73-4 (3R,6R,7S,8aS)-7-(p-fluorophenyl)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 277744-02-2 (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine 
• 277743-96-1 (3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol 
• 179179-80-7 (+/-)-trans-4-(4-Fluoro-phenyl)-3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester 
• 277743-71-2 (3R,6R,7S,8aS)-6-(methoxycarbonyl)-5-oxo-3,7-diphenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 277743-99-4 (3R,4S)-3-Methanesulfonyloxymethyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 277743-94-9 (3R,4S)-1-[(1R)-2-hydroxy-1-phenylethyl]-4-phenyl-3-piperidinemethanol 
• 179179-79-4 tert-butyl (+)-(3R,4S)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 277743-97-2 (3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol 
• 59859-58-4 femoxetine 
• 61869-08-7 paroxetine 

Relevant articles and documents

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.