Synthesis of N-substituted pyrrolin-2-ones

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 291-294

  Mattern, Ralph Heiko ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030033598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02267-8     Document Type: Article

References (13)

1. Pettit, G.R.; Kamano, Y.; Herald, C.L.; Fujii, Y.; Kizu, H.; Boyd, M.R.; Boettner, F.E.; Doubek, D.L., Schmidt, J.M., Chapuis, J-C.; Michel, C. Tetrahedron 1993, 49, 9151.
2. Koehn, F.E.; Longley, R.E.; Reed, J.K. J. Nat. Prod. 1992, 55 (5), 613.
3. Moore, R.E.; Entzeroth, M. Phytochemistry 1988, 27 (10), 3101.
4. Koehn, F.E.; McConnell, O.J.; Longley, R.E.; Sennett, S.S.; Reed, J.K. J. Med. Chem. 1994, 37, 3181.
5. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc. Perkin Trans. 1987, 1177.
6. Schmidt, U; Riedl, B.; Haas, G.; Griesser, H.; Vetter, A.; Weinbrenner, S. Synthesis 1993, 216-220.
7. Rothe, M; Toth, T; Daser, R. Chem. Ber. 1966, 99, 3820.
8. 4. After filtration the solvent was removed in vacuo and the crude product was purified by chromatography on silica gel using ethyl acetate/heptane 4:1 as solvent. 520 mg of the 1-carbobenzoxy-5-methylpyrrolin-2-one (4, 62.1 %) and 435 mg 1-carbobenzoxy-4-butyloxycarbonyloxy-5-methylpyrrolidin-2-one (5, 34.6 %) were obtained.
9. 3).
10. 3): 13.2, 13.9, 20.6, 27.3, 36.3, 55.7, 60.0, 67.8, 68.9, 82.9, 127.9, 128.1, 128.3, 134.8, 150.5, 152.2, 169.0;
11. 3).
12. 3).
13. 3): 43.8, 58.2, 67.5, 125.2, 127.8, 128.0, 128.3, 135.1, 150.5, 152.4, 168.4.