Abstract
A C18 1-pyrroline fatty ester, methyl 8-(5-hexyl-2-pyrrolin-1-yl)octanoate (1), was prepared from methyliso-ricinoleate. The C=N bond of the pyrroline ring was oxidized bym-chloroperoxy-benzoic acid to yield a mixture of oxaziridine isomers 2a,2b, which decomposed during gas chromatographic analysis to a 2,5-disubstituted pyrrole derivative, methyl 8-(5-hexyl-1H-pyrrole-2-)octanoate (3). Compound 3 was also obtained by reaction of 2a,2b with dilute HCl in methanol. Reaction of compound 1 with iodo-methane formed anN-methyl iminium iodide intermediate 4, which on reduction with sodium borohydride furnished a mixture ofcis/trans-N-methyl-2,5-disubstituted pyrrolidine derivatives, methyl 8-(cis/trans-5-hexyl-N-methyl-pyrrolidine-2-)octanoates 5a,5b. Reduction of compound 1 with NaBH4 gave a mixture ofcis/trans-isomers of 2,5-disubstituted pyrrolidine derivatives, methyl 8-(5-hexyl-pyrrolidine-2-)octanoates 6a,6b. Acetylation of compounds 6a,6b with acetic anhydride furnished the correspondingN-acetyl pyrrolidines 7a,7b. When compound 1 was treated with perchloric acid, the corresponding iminium perchlorate derivative, methyl 8-(5-hexyl-1-pyrrolinium perchlorate-2-)octanoate 8 was obtained. The structures of the various derivatives were characterized by a combination of chromatographic, mass spectral and spectroscopic techniques.
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Abbreviations
- 13C NMR:
-
13C nuclear magnetic resonance
- GC:
-
gas chromatography
- GC/MS:
-
gas chromatography/mass spectrometry
- ECL:
-
equivalent chain length
- 1H NMR:
-
1H nuclear magnetic resonance
- IR:
-
infrared
- TLC:
-
thin-layer chromatography
- Solvent A:
-
light petroleum (b.p. 40–60°C)/diethyl ether (4∶1, v/v)
- Solvent B:
-
light petroleum (b.p. 40–60°C)/diethyl ether (7∶3, v/v)
- Solvent C:
-
light petroleum (b.p. 40–60°C)/diethyl ether (1∶1, v/v)
- Solvent D:
-
light petroleum (b.p. 40–60°C)/diethyl ether (2∶3, v/v)
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Lie Ken Jie, M.S.F., Syed-Rahmatullah, M.S.K. Preparation and some spectroscopic properties ofN-heterocyclic derivatives of a novel 1-pyrroline C18 fatty ester. Lipids 26, 842–846 (1991). https://doi.org/10.1007/BF02536167
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DOI: https://doi.org/10.1007/BF02536167