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Clarke, Paul A.; Zaytzev, Andrey V.; Whitwood, Adrian C. (2007)
Languages: English
Types: Article
Subjects:
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. Fo r rece nt re views on the synthesis of pipe ridine s see : Lasc hat, S.; Dickner, T. Synthe sis 2000, 1781 . Weintraub, P. M.; Sabol, J. S.; Kane, J. M; Borche rding, D. R. Tetrahed ron 2003, 59, 2953. Buffat, M. G. P . Te trahed ron 2004 , 60, 1701.
    • 2. Watson, P. S.; Jiang, B.; and Scott, B. Org . Lett. 2000 , 2, 3679.
    • 3. Clarke , P . A.; Santo s, S.; Martin, W. H. C. Gre en Chem. 2007 , 9, 438.
    • 4. (a) Tro st, B. M.; Science 1991 , 254, 1471 . (b) Tro st, B. M. Ange w. Che m. In t. Ed. 1995 , 34 , 259 .
    • 5. (a) We nder, P. A.; Bi, F . C.; Gambe r, G. G.; Gosse lin, F.; Hubb ard, R. D.; Sc anio , M. J. C.; Sun, R .; Williams, T. J.; Zh ang, L. Pure Appl. Chem. 2002, 74, 25. (b) Wende r, P. A.; Handy, S. T.; and Wright, D. L. Chem. Ind. (London ) 1997 , 765. (c ) We nde r, P. A.; Miller, B. L. Organ ic Synthe sis: Theory and Applica tions; Hudlic ky, T. Ed.; JAI: Gree nwic h, 1993; Vol. 2 , pp 27 - 66 .
    • 6. Clarke , P. A.; Martin, W. H. C.; Hargreave s, J. M.; Wilson, C.; Blake, A. J. Ch em. Commun . 2005 , 1061 . Clarke , P. A.; Martin, W. H. C.; Hargreave s, J. M.; Wilson, C.; Blake, A. J. Org. Biomol. Che m. 2005 , 3 , 3551 .
    • 7. Prajapati, D.; Gohain, M. Be ilste in J. Org . Chem. 2006 , 2:11 .
    • 8. Lo h, T.-P .; Wei, L .-L. Tetrahedron Le tt. 1998, 39, 323.
    • 9. Lo h, T.-P .; Wei, L .-L. Synlett 1998, 975 .
    • 10. General procedure for the P ASE synthe sis o f pipe ridines: Methyl ace to acetate (2 mmo l), aldehyde (4 mmol) and aniline (4 mmo l) were dissolved in ac etonitrile (4 ml) and InCl3 (0 .147 g, 0.67 mmol) was intro duced. The reactio n mixture was stirre d at room temperature for 24 or 48 h. The pro duct was iso lated by filtration of the prec ipitate and washing with a sm all amo unt o f ac etonitrile o r, if no precipitation occurre d, the so lvent was e vaporated and the residue was purified by flash co lumn c hromatography on silica gel (Et2O – Petro l). Co mpo und 4i νmax/c m-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 (2 H, d, J 7 .5 , Ar), 7 .10-7.05 (5 H, 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 .1 5 (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), 3 3.6 (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 require s 461.2224).
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