Synthesis, separation, and resolution of cis - and trans -3-ethylproline
dc.contributor.author | Tiba, Omar | en_US |
dc.contributor.author | Overberger, Charles Gilbert | en_US |
dc.date.accessioned | 2006-04-28T18:18:23Z | |
dc.date.available | 2006-04-28T18:18:23Z | |
dc.date.issued | 1987-12 | en_US |
dc.identifier.citation | Tiba, Omar; Overberger, C. G. (1987)."Synthesis, separation, and resolution of cis - and trans -3-ethylproline." Journal of Polymer Science Part A: Polymer Chemistry 25(12): 3437-3458. <http://hdl.handle.net/2027.42/38825> | en_US |
dc.identifier.issn | 0887-624X | en_US |
dc.identifier.issn | 1099-0518 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/38825 | |
dc.description.abstract | The synthesis, separation, and optical resolution of cis - and trans -3-ethylproline are described. Two different approaches were employed: (1) The Michael addition reaction of 2-pentenal with diethyl-N-carbobenzyloxyaminomalonate gave the intermediate 3-ethyl-5-hydroxy-N-benzyloxypyrrolidine. Hydrogenolysis of this intermediate followed by acid hydrolysis gave a mixture of cis - and trans -3-ethylproline. Separation of the isomers was accomplished by selective saponification of N-( p -toluenesulfonyl)- cis - and trans -3-ethylproline methyl esters using 0.25 N methanolic sodium hydroxide. (2) The Michael condensation of diethyl acetamidomalonate with 2-pentenoic acid ethyl ether produced the intermediate 5,5-bis(ethoxycarbonyl)-4-ethylpyrrolidine. Partial saponification followed by decarboxylation afforded a mixture of cis - and trans -isomers of ethyl-3-ethylpyroglutamate. The diastereoisomers were separated using low temperature fractional crystallization. Reduction of these isomers and tosylation in situ afforded the corresponding N-( p -toluenesulfonyl)- cis - and trans -3-ethylprolinols. Chromic acid oxidation gave N-( p -toluenesulfonyl)- cis - and trans -3-ethylproline. Reaction of these tosylates with 30% hydrogen bromide in acetic acid gave cis - and trans -3-ethylproline. Both optically active isomers of D(+)-and L(-)- trans -3-ethylproline were successfully resolved using (+)-dibenzoyl- D -tartaric acid and (-)-dibenzoyl- L -tartaric acid as resolving agents. The absolute configurations of the optically active isomers were determined by circular dichroism spectroscopy. | en_US |
dc.format.extent | 1412656 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | John Wiley & Sons, Inc. | en_US |
dc.subject.other | Chemistry | en_US |
dc.subject.other | Polymer and Materials Science | en_US |
dc.title | Synthesis, separation, and resolution of cis - and trans -3-ethylproline | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Chemistry and the Macromolecular Research Center, The University of Michigan, Ann Arbor, Michigan 48109 | en_US |
dc.contributor.affiliationum | Department of Chemistry and the Macromolecular Research Center, The University of Michigan, Ann Arbor, Michigan 48109 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/38825/1/080251224_ftp.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1002/pola.1987.080251224 | en_US |
dc.identifier.source | Journal of Polymer Science Part A: Polymer Chemistry | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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