78187-36-7

Upstream product

• 1187-81-1 5-chloro-3-methylpentane-2-one 
• 78584-60-8 cis-2-(p-chlorophenyl)-3-(1,1-ethylenedioxyethyl)-1,3-dimethylpyrrolidine 
• 78584-66-4 cis-2-(p-chlorophenyl)-3-(1,1-ethylenedioxyethyl)-3-methylpyrrolidine 
• 78584-61-9 cis-3-acetyl-2-(p-chlorophenyl)-1,3-dimethylpyrrolidine 
• 78597-57-6 4,4-ethylenedioxy-3-methyl-N-(p-chlorobenzylidene)pentylamine 
• 78584-58-4 cis-3-acetyl-2-(p-chlorophenyl)-3-methylpyrrolidine 
• 78584-54-0 5-phthalimido-3-methyl-2-pentanone ethylene acetal 
• 78584-51-7 2-(3-methyl-4-oxopentyl)isoindoline-1,3-dione 
• 78584-55-1 5-amino-3-methyl-2-pentanone ethylene acetal 
• 1123-19-9 3-acetyl-3-methyl-dihydro-furan-2-one 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 78584-63-1 cis-(p-chlorophenyl)-3-(2-hydroxy-2-propyl)-1,3-dimethylpyrrolidine 

Downstream Products

• 78187-41-4 cis-3-isopropyl-1,3-dimethyl-2-phenylpyrrolidine 

Relevant academic research and scientific papers

Reinvestigation of the Stevens Rearrangement of 1-Benzyl-1,3,4-trimethyl-1,2,5,6-tetrahydropyridinium Salts II. Synthesis of 2-Aryl-3-isopropenyl-1,3-dimethylpyrrolidines

cis-2-Aryl-3-isopropenyl-1,3-dimethylpyrrolidines IIa and IIb have been synthesized by an unambiguous way, thus confirming the structure of the methylene derivatives obtained as by-products in the Stevens rearrangement of 1-benzyl-1,3,4-trimethyl-1,2,5,6-tetrahydropyridinium salts Ia and Ib.The synthesis is based on the acid-induced intramolecular cyclization between an iminium salt and the α-position of a ketal group.Thus, condensation between amino ketal XXI, prepared via Gabriel synthesis from 5-chloro-3-methyl-2-pentanone, and the appropriate aldehyde afforded imines XXI.Their treatment with dry hydrogen chloride followed by acid hydrolysis and methylation gave 3-acetylpyrrolidines IV, which were transformed into the isopropenyl derivatives II by reaction with methyl-lithium and further dehydration.