Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates

Tetrahedron

Volumn 65, Issue 27, 2009, Pages 5393-5401

  Blanco Ania, Daniel ^a   Hermkens, Pedro H H ^b   Sliedregt, Leo A J M ^c   Scheeren, Hans W ^a   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b MERCK RESEARCH LABORATORIES   (United States)

^c Solvay Pharmaceuticals Inc   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; ALDEHYDE; AZOMETHINE YLIDE; CARBOXYLIC ACID DERIVATIVE; CUCURBITINE DERIVATIVE; ESTER DERIVATIVE; IMINE; NATURAL PRODUCT; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIASTEREOISOMER; KNOEVENAGEL CONDENSATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 66349083498     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.059     Document Type: Article

References (43)

1. Morimoto Y., and Achiwa K. Chem. Pharm. Bull. 35 (1987) 3845-3849
2. Thiery, V.; Guillaumet, G.; Andre, P. Process for synthesis of cucurbitine (cucurbitin) using 1-benzyl-3-pyrrolidone as starting material. FR 2673626, September 11, 1992;
3. Chem. Abstr. 118 (1993) 81435
4. von Bohlen und Halbach O., and Dermietzel R. Neurotransmitters and Neuromodulators: Handbook of Receptors and Biological Effects. 2nd ed. (2006), Wiley-VCH, Weinheim, Germany
5. Campbell L.M. Int. J. Clin. Pract. 56 (2002) 783-790
6. Skidmore, I. F.; Lunts, L. H. C.; Finch, H.; Naylor, A. Phenethanolamin-Verbindungen, Verfahren zu Ihrer Herstellung und Diese Verbindungen Enthaltende Arzneimittel. DE 3414752, October 18, 1984;
7. Chem. Abstr. 102 (1985) 95383
8. Johnson D.S., and Li J.J. The Art of Drug Synthesis (2007), Wiley-Interscience, New York, NY
9. Yardley J.P., Husbands G.E.M., Stack G., Butch J., Bisckler J., Moyer J.A., Muth E.A., Andree T., Fletcher III H., James M.N.G., and Sieleck A.R. J. Med. Chem. 33 (1990) 2899-2905
10. Husbands, G. E. M.; Yardley, J. P.; Muth, E. A. 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives. U.S. Patent 4,535,186, August 13, 1985;
11. Chem. Abstr. 102 (1985) 5895
12. Carlucci, D. R.; Aitken, M. IMS Intelligence.360, 2007. IMS Health Home Page. http://www.imshealth.com/ims/portal/front/articleC/0,2777,6266_41382706_ 81567488,00.html (accessed June 20, 2008).
13. Shulgin A., and Shulgin A. Pihkal: a Chemical Love Story (1991), Transform, Berkeley, CA
14. Shulgin A., and Shulgin A. Tihkal: the Continuation (1997), Transform, Berkeley, CA
15. Mamoun O., Benhaoua H., Danion-Bougot R., and Danion D. Synth. Commun. 25 (1995) 1295-1302
16. Benhaoua H., Danion-Bougot R., and Carrie R. Bull. Soc. Chim. Fr. (1989) 409-412
17. Benhaoua H., Piet J.C., Danion-Bougot R., Toupet L., and Carrie R. Bull. Soc. Chim. Fr. (1987) 325-338
18. Hohenlohe-Oehringen K., and Bretschneider H. Monatsh. Chem. 94 (1963) 1241-1246
19. Zen S., Koyama M., and Koto S. Organic Synthesis Collect. Vol. 6 (1988), Wiley & Sons, New York, NY 1976, Vol. 55, 77, 797-799
20. For a review about Knoevenagel condensation, see:. Tietze L.F., and Beifuss U. The Knoevenagel Reaction. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 341-394
21. Kuster G.J.T., van Berkom L.W.A., Kalmoua M., van Loevezijn A., Sliedregt L.A.J.M., van Steen B.J., Kruse C.G., Rutjes F.P.J.T., and Scheeren H.W. J. Comb. Chem. 8 (2006) 85-94
22. Sato K., Tarui A., Matsuda S., Omote M., Ando A., and Kumadaki I. Tetrahedron Lett. 46 (2005) 7679-7681
23. Moonen K., and Stevens C.V. Synthesis 20 (2005) 3603-3612
24. Babievskii K.K., Belikov V.M., Vinograndova A.I., and Latov V.K. J. Org. Chem. U.S.S.R. 9 (1973) 1722-1725
25. To differentiate the (Z/E)-isomers by X-ray crystallography, see:. He L.W., Srikanth G.S.C., and Castle S.L. J. Org. Chem. 70 (2005) 8140-8147
26. Fornicola R.S., Oblinger E., and Montgomery J. J. Org. Chem. 63 (1998) 3528-3529
27. These conditions were also used with aldehyde 10e, but the yield was lower than the one obtained with the imine procedure.
28. Kleinpeter E. J. Serb. Chem. Soc. 71 (2006) 1-17
29. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2809
30. Snider B.B., Ahn Y., and O'Hare S.M. Org. Lett. 3 (2001) 4217-4220
31. 4 to the reaction mixture solved the problem.
32. For examples of Krapcho reaction with α-nitro esters, see:
33. Dahnz A., and Helmchen G. Synlett (2006) 697-700
34. Peel M.R., Sternbach D.D., and Johnson M.R. J. Org. Chem. 56 (1991) 4990-4993
35. Smith M.B., and March J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 6th ed. (2007), John Wiley & Sons, Hoboken, NJ
36. 3N to prevent amide formation
37. The reason for this activation is unclear.
38. Yashin N.V., Averina E.B., Grishin Y.K., Kuznetsova T.S., and Zefirov N.S. Synthesis (2006) 279-284
39. For a reduction of this kind on an α-nitro ester, see:. Krishnamoorthy P., Sivappa R., Du H.W., and Lovely C.J. Tetrahedron 62 (2006) 10555-10566
40. The reaction gave also traces of products from elimination of the nitro group {A figure is presented} 17a-e (<0.5%). Once the nickel enolate is formed (see reaction sequence below), it eliminates in a Saegusa-type reaction fashion. For a discussion on the mechanism of the Saegusa reaction, see. Porth S., Bats J.W., Trauner G.G., and Mulzer J. Angew. Chem., Int. Ed. 38 (1999) 2015-2016 In some cases, for Ar=3,5-dimethoxyphenyl and 3,4-methylenedioxyphenyl, products from subsequent aromatization {A figure is presented} 18b-c (<0.5%) were also found
41. For a radical reduction of α-nitro nitriles, α-nitro esters, and α-nitro ketones, see:. Ono N., Tamura R., and Kaji A. J. Am. Chem. Soc. 105 (1983) 4017-4022
42. For a discussion on the radical reduction of thiols and sulfides with Raney nickel, see:. Hauptmann H., and Walter W.F. Chem., Rev. 62 (1962) 347-404
43. For an example of nickel C/O-enolate equilibration, see:. Cámpora J., Maya C.M., Palma P., Carmona E., Gutiérrez E., Ruiz C., Graiff C., and Tiripicchio A. Chem.-Eur. J. 11 (2005) 6889-6904