Acid-catalyzed rearrangement of 1-benzyl-2-methyl-3-piperidone to 1-benzyl-2-acetylpyrrolidine

Tetrahedron

Volumn 62, Issue 26, 2006, Pages 6361-6369

  Zhao, Shengyin ^a   Jeon, Heung Bae ^a   Nadkarni, Durgesh V ^a   Sayre, Lawrence M ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

Clemmensen reduction; Piperidone; Pyrrolidone; Rearrangement

Indexed keywords

1 BENZYL 2 ACETYLPYRROLIDINE; 1 BENZYL 2 METHYL 3 PIPERIDONE; 3 HYDROCY 2 METHYLPYRIDINE; HYDROCHLORIC ACID; PICOLINE DERIVATIVE; PIPERIDONE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 33646814774     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.038     Document Type: Article

References (33)

1. Weintraub P.M., Sabol J.S., Kane J.M., and Borcherding D.R. Tetrahedron 59 (2003) 2953
2. O'Hagan D. Nat. Prod. Rep. 17 (2000) 435
3. Plunkett A.O. Nat. Prod. Rep. 11 (1994) 581
4. Hu L.Y., Ryder T.R., Rafferty M.F., Feng M.R., Lotarski S.M., Rock D.M., Sinz M., Stoehr S.J., Taylor C.P., Weber M.L., Bowersox S.S., Miljanich G.P., Millerman E., Wang Y.X., and Szoke B.G. J. Med. Chem. 42 (1999) 4239
5. LaRoche S.M., and Helmers S.L. JAMA 291 (2004) 605
6. Tepper S.J., Rapoport A.M., and Sheftell F.D. Arch. Neurol. 59 (2002) 1084
7. Sayre L.M., Engelhart D.A., Nadkarni D.V., Babu M.K.M., Klein M.E., and McCoy G. Xenobiotica 25 (1995) 769
8. Sayre L.M., Engelhart D.A., Venkataraman B., Babu M.K.M., and McCoy G.D. Biochem. Biophys. Res. Commun. 179 (1991) 1368
9. Stevens C.L., Pillai P.M., Munk M.E., and Taylor K.G. In: Thyagarajan B.S. (Ed). Mechanisms of Molecular Migrations (1968), Interscience, New York, NY 271
10. Duhamel P., Kotera M., Monteil T., and Marabout B. J. Org. Chem. 54 (1989) 4419
11. Leonard N.J., and Ruyle W.V. J. Am. Chem. Soc. 71 (1949) 3094
12. Leonard N.J., and Berthel Jr. E. J. Am. Chem. Soc. 72 (1950) 3632
13. Leonard N.J., and Wildman W.C. J. Am. Chem. Soc. 71 (1949) 3089
14. Rearrangement of optically active 1,2-dimethyl-2-ethyl-3-piperidione gave racemic 1-methyl-2-sec-butylpyrrolidine, indicating that there must be complete cleavage of the C-N bond at some point in the rearrangement:. Leonard N.J., Sentz R.C., and Middleton W.J. J. Am. Chem. Soc. 75 (1953) 1674
15. Brunner H., Kagan H.B., and Kreutzer G. Tetrahedron: Asymmetry 14 (2003) 2177
16. Compain P., Goré J., and Vatèle J.-M. Tetrahedron 52 (1996) 6647
17. Ooi T., Saito A., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 3220
18. Hagishita S., Yamada M., Shirahase K., Okada T., and Murakami Y. J. Med. Chem. 39 (1996) 3636
19. Lounasmaa M., Karvinen E., Koskinen A., and Jokela R. Tetrahedron 43 (1987) 2135
20. Goes A.D.S., Ferroud C., and Santamaria J. Tetrahedron Lett. 36 (1995) 2235
21. Macchia B., Macchia M., Martinelli A., Martinotti E., Orlandini E., Romagnoli F., and Scatizzi R. Eur. J. Med. Chem. 32 (1997) 231
22. We have shown independently that autoxidation of 2, accelerated by base, results in oxygenation and breakdown to 14 and acetic acid: Nadkarni, D. V.; Babu, M. K. M.; Jeon, H.-B.; Sayre, L. M. Unpublished.
23. Sanders E.B., Secor H.V., and Seeman J.I. J. Org. Chem. 43 (1978) 324
24. Li J.J. Name Reactions: A Collection of Detailed Reaction Mechanisms. 2nd ed. (2003), Springer, Berlin
25. Fleming S.A., Carroll S.M., Hirschi J., Liu R., Pace J.L., and Redd J.T. Tetrahedron Lett. 45 (2004) 3341
26. Hofmann T., and Schieberle P. J. Agric. Food Chem. 46 (1998) 2270
27. De Kimpe N., and Stevens C. Tetrahedron 51 (1995) 2387
28. Ozdowska Z. Pol. J. Chem. 52 (1978) 385
29. Emmett G.C., Cain G.A., Estrella M.J., Holler E.R., Piecara J.S., Blum A.M., Mical A.J., Teleha C.A., and Wacker D.A. Synthesis 1 (2005) 92
30. 2 in the latter averts partial eclipsing interactions:. Carey F.A., and Sundberg R.J. Advanced Organic Chemistry, Part A: Structure and Mechanism. 4th ed. (2000), Kluwer Academic, New York, NY p 172
31. Schneider H.-J., and Thomas F. J. Am. Chem. Soc. 102 (1980) 1424
32. Di Vona M.L., and Rosnati V. J. Org. Chem. 56 (1991) 4269
33. Julia T. Bull. Soc. Chim. Fr. (1958) 661