33598-27-5

Upstream product

• 123-75-1 pyrrolidine 
• 623-43-8 crotonic acid methyl ester 
• 55212-79-8 (E)-3-pyrrolidinobut-2-enoic acid methyl ester 
• 103-26-4 Methyl cinnamate 
• 623-43-8 methyl crotonate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 355-25-9 perfluorobutane 
• 53708-07-9 perfluoro(N-propylpyrrolidine) 
• 123320-68-3 perfluoro(3-pyrrolidino-n-butyryl fluoride) 

Relevant academic research and scientific papers

Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions

The efficient and very simple conjugate addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in the presence of catalytic amount of silicon tetrachloride is reported. The reaction of aryl and alkyl amines with different Michael acceptors gave the corresponding Michael adducts with simple catalyst and good to excellent yields. Georg Thieme Verlag Stuttgart New York.

Hydrogenation of β-N-substituted and β-N,N-disubstituted enamino esters in the presence of iridium(I) catalyst

Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50°C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields. Georg Thieme Verlag Stuttgart.

Air- and moisture-stable cationic (diphosphine)palladium(II) complexes as hydroamination catalysts X-ray crystal structures of two complexes

A series of cationic (diphosphine)palladium(II) complexes have been prepared and fully characterized, including two crystal structures. These complexes were evaluated as catalysts for the hydroamination of acyclic alkenes. The reactivity of the catalysts is dependent on the nature of the diphosphine ligand and the substituents on the amine and alkene substrates.

Synthesis and analgesic activity of N-aryl/arylalkyl 3-(1- pyrrolidinyl/piperidinyl)butyramides

Conjugate addition of pyrrolidine or piperidine to methyl crotonate, and hydrolysis of the resulting methyl butyrates gave the (±)-3-pyrrolidino or piperidinobutyric acids 17 and 18, respectively. Coupling of these racemic acids to arylalkylamines, L-phen

Anthraquinone-photocatalysed addition of amines toα,β-unsaturated esters: a novel route to indolizidone, pyrrolizidone and related ring systems

The indolizidone 9, the pyrrolizidone 14, a mixture of heliotridone 15a and pseudoheliotridone 15b and the lactam 19 have been synthesized in a one-step anthraquinone-photocatalysed reaction of the corresponding amines, piperidine 1, pyrrolidine 10 and morpholine 16, with α,β-unsaturated esters.

ENAMINE CHEMISTRY-XXV REDUCTION OF ENAMINONONES BY LiAlH4 AND NaBH4 SYNTHESIS OF α,β-UNSATURATED ALDEHYDES

Cyclohexanone, 2-methyl-cyclohexanone and 4-methyl-cyclohexanone, 1, were transformed into the enaminones 4a-4e by the following two routes: (A): Acylation of the enamines, 2, derived from 1 and secondary amines (pyrrolidine, morpholine and piperidine) by ethyl chloroformate, and (B): Condensation of 1 with diethyl oxalate, giving the β-ketoesters 3, followed by reaction with the secondary amines.Ethyl 2(-1-pyrrolidinyl)-1-cyclopentene-1-carboxylate. 4f, and methyl 3-(1-pyrrolidinyl)-2-buteonate, 4g, were prepared from ethyl 2-oxo-1-cyclopentanecarboxylate and ethyl 3-oxo-butanoate, respectively, by condensation with pyrrolidine.Reduction of 4a by LAH afforded 1-cyclohexen-1-carboxaldehyde, 5a, 1-cyclohexene-1-methanol, 6a, and 1-(1-cyclohexene-1-methyl)pyrrolidine, 7a, in yields depending on the molar ratio of LAH/4a.Reduction of 4f by LAH gave cyclopenten-1-methanol, 6b, 1-(1-cyclopentene-1-methyl)pyrrolidine, 7b, and ethyl-2(1-pyrrolidinyl)-1-cyclopentanecarboxylate, 8b.Compound 4g, when reduced with LAH, yielded methyl 3-(1-pyrrolidinyl) butanoate, 8c (main product) and 1-(2-butenyl)pyrrolidine, 7c (minor).Reduction of 4 by NaBH4 afforded exlusively the saturated β-aminoesters, 8, in high yields.The reductions with LAH and NaBH4 are rationalized in terms of the HSAB principle.