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Languages: English
Types: Article
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The diastereoselective pot, atom and step economic (PASE) synthesis of highly functionalized piperidines has been realized. The procedure simply involves mixing methyl acetoacetate, 2 equiv of aldehyde and 2 equiv of aniline together in the presence of InCl3. In most cases the piperidine precipitates out of solution. (c) 2007 Elsevier Ltd. All rights reserved.
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    • 1. For recent reviews on the synthesis of piperidines see: Laschat, S.; Dickner, T. Synthesis 2000, 1781. Weintraub, P. M.; Sabol, J. S.; Kane, J. M; Borcherding, D. R. Tetrahedron 2003, 59, 2953. Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
    • 2. Watson, P. S.; Jiang, B.; and Scott, B. Org. Lett. 2000, 2, 3679.
    • 3. Clarke, P. A.; Santos, S.; Martin, W. H. C. Green Chem. 2007, 9, 438.
    • 4. (a) Trost, B. M.; Science 1991, 254, 1471. (b) Trost, B. M. Angew. Chem. Int. Ed. 1995, 34, 259.
    • 5. (a) Wender, P. A.; Bi, F. C.; Gamber, G. G.; Gosselin, F.; Hubbard, R. D.; Scanio, M. J. C.; Sun, R .; Williams, T. J.; Zhang, L. Pure Appl. Chem. 2002, 74, 25. (b) Wender, P. A.; Handy, S. T.; and Wright, D. L. Chem. Ind. (London) 1997, 765. (c) Wender, P. A.; Miller, B. L. Organic Synthesis: Theory and Applications; Hudlicky, T. Ed.; JAI: Greenwich, 1993; Vol. 2, pp 27- 66.
    • 6. Clarke, P. A.; Martin, W. H. C.; Hargreaves, J. M.; Wilson, C.; Blake, A. J. Chem. Commun. 2005, 1061. Clarke, P. A.; Martin, W. H. C.; Hargreaves, J. M.; Wilson, C.; Blake, A. J. Org. Biomol. Chem. 2005, 3, 3551.
    • 7. Prajapati, D.; Gohain, M. Beilstein J. Org. Chem. 2006, 2:11.
    • 8. Loh, T.-P.; Wei, L.-L. Tetrahedron Lett. 1998, 39, 323.
    • 9. Loh, T.-P.; Wei, L.-L. Synlett 1998, 975.
    • 10. General procedure for the PASE synthesis of piperidines: Methyl acetoacetate (2 mmol), aldehyde (4 mmol) and aniline (4 mmol) were dissolved in acetonitrile (4 ml) and InCl3 (0.147 g, 0.67 mmol) was introduced. The reaction mixture was stirred at room temperature for 24 or 48 h. The product was isolated by filtration of the precipitate and washing with a sm all amount of acetonitrile or, if no precipitation occurred, the solvent was evaporated and the residue was purified by flash column chromatography on silica gel (Et2O - Petrol). Compound 4i νmax/cm-1 (KBr) 3446, 2918, 2850, 1662, 1588, 1503, 1254, 1078; δH (500 MHz, CDCl3) 10.26 (1H, s, NH), 7.33-7.25 (7H, m, Ar), 7.21 (1H, m, Ar), 7.17 (2H, d, J 7.5, Ar), 7.10-7.05 (5H, m, Ar), 6.61 (1H, t, J 7.0, Ar), 6.53 (2H, d, J 8.5, Ar), 6.46 (1H, s, 2-H), 6.30-6.28 (2H, m, Ar), 5.15 (1H, m, 6-H), 2.88 (1H, dd, J 15.3 and 5.8, 5-Ha), 2.77 (1H, dd, J 15.3 and 2.3, 5- Hb); δH (125 MHz, CDCl3) 168.6 (C, COOCH3), 156.3 (C), 146.9 (C), 143.9 (C), 142.7 (C), 137.8 (C), 128.9 (CH), 128.8 (CH), 128.6 (CH), 128.2 (CH), 127.1 (CH), 126.6 (CH), 126.4 (CH), 126.3 (CH), 125.9 (CH), 125.8 (CH), 116.1 (CH), 112.9 (CH), 97.9 (C, C-3), 58.2 (CH, C-6), 55.1 (CH, C-2), 51.0 (CH3, COOCH3), 33.6 (CH2, C-5); MS (ES) 461 (M+H+, 12) , 386 (8), 280 (34), 182 (100), 150 (10), 121 (23), 106 (36), 94 (31); HRMS (ES) 461.2224 (M + H+. C31H29N2O2 requires 461.2224).
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