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Volumn , Issue 10, 1999, Pages 1253-1255

Synthesis of the potent analgesic compound (±)-epibatidine using an orchestrated multi-step sequence of polymer supported reagents

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EID: 33746458894     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901802f     Document Type: Article
Times cited : (129)

References (41)
  • 2
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    • ed. G. A. Cordell, Academic Press, New York, 1995,vol. 46,pp. 95-125.
    • For a review see; C. Szântay, Z. Kardos-Balogh and C. Szântay, Jr., in The Alkaloids, ed. G. A. Cordell, Academic Press, New York, 1995,vol. 46,pp. 95-125.
    • The Alkaloids
    • Szântay, C.1    Kardos-Balogh, Z.2    Szântay Jr., C.3
  • 19
    • 37049109813 scopus 로고    scopus 로고
    • 1977,815; borohydride on Amberlyst (3 mmol g"') was used as supplied by Fluka.
    • H. W. Gibson and F. C. Bailey, J. Chem. Soc., Chem. Commun., 1977,815; borohydride on Amberlyst (3 mmol g"') was used as supplied by Fluka.
    • J. Chem. Soc., Chem. Commun.
    • Gibson, H.W.1    Bailey, F.C.2
  • 27
    • 0005966516 scopus 로고    scopus 로고
    • 1986,46 but in our hands, Amberlite IRA-420 (OH" form, used as supplied by Aldrich) proved to be much more successful.
    • The use of Amberlyst A-21 for Henry reactions has been previously described (G. Rosini, R. Ballini and M. Petrini, Synthesis, 1986,46) but in our hands, Amberlite IRA-420 (OH" form, used as supplied by Aldrich) proved to be much more successful.
    • Synthesis
    • Rosini, G.1    Ballini, R.2    Petrini, M.3
  • 28
    • 33746462572 scopus 로고    scopus 로고
    • 10 Reagents were encapsulated into pouches by Cambridge Combinatorial, Cambridge, UK.
    • , vol.10
  • 29
    • 33746454533 scopus 로고    scopus 로고
    • 1981,5-4,631; aminomethylpyridine on polystrene as supplied by Fluka (2 mmol g~') was dried overnight in vacua (<1 mmHg) at 60 °C prior to use.
    • S. Shinkai, H. Tsuji, Y. Kara and O. Manabe, Bull. Chem. Soc. Jpn., 1981,5-4,631; aminomethylpyridine on polystrene as supplied by Fluka (2 mmol g~') was dried overnight in vacua (<1 mmHg) at 60 °C prior to use.
    • Bull. Chem. Soc. Jpn.
    • Shinkai, S.1    Tsuji, H.2    Kara, Y.3    Manabe, O.4
  • 37
    • 0027520152 scopus 로고    scopus 로고
    • 1993,23,3047 [with Ni(OAc)2-4H2O]
    • Modification of borohydride exchange resin with inorganic reagents to effect the reduction of aliphatic nitro groups to amines has been previously reported; (a) N. M. Yoon, J. Choi and Y. S. Shon, Synth. Commun., 1993,23,3047 [with Ni(OAc)2-4H2O];
    • Synth. Commun.
    • Yoon, N.M.1    Choi, J.2    Shon, Y.S.3
  • 38
    • 0000180963 scopus 로고    scopus 로고
    • 1997,70,1101 [with CuSO4V SHjO]. We have found that addition of polymer supported borohydride (on Amberlite IRA-400 as supplied by Aldrich) to a solution of NiCl2-6H2O in MeOH (prepared by sonnication) was far superior for this transformation.
    • (b) T. B. Sim and N. M. Yoon, Bull. Chem. Soc. Jpn., 1997,70,1101 [with Cu(SO4V SHjO]. We have found that addition of polymer supported borohydride (on Amberlite IRA-400 as supplied by Aldrich) to a solution of NiCl2-6H2O in MeOH (prepared by sonnication) was far superior for this transformation.
    • Bull. Chem. Soc. Jpn.
    • Sim, T.B.1    Yoon, N.M.2


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