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Volumn 73, Issue 3, 2008, Pages 1150-1153

An efficient method for the synthesis of nitropiperidones

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC PURIFICATION; MICHAEL ADDITION; NITROPIPERIDONES; UNSATURATED ESTERS;

EID: 38849133572     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702130a     Document Type: Article
Times cited : (26)

References (45)
  • 8
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    • (d) For a review, see: Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
    • (2004) Tetrahedron , vol.60 , pp. 1701
    • Buffat, M.G.P.1
  • 12
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    • Edmondson, S. D.; Mastracchio, A.; Cox, J. M. PCT Int. Appl. WO2006058064, 2006.
    • (b) Edmondson, S. D.; Mastracchio, A.; Cox, J. M. PCT Int. Appl. WO2006058064, 2006.
  • 21
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    • 4 Davis' protocol (a) with slight modifications in the workup (b): (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13 and references cited therein,
    • 4 Davis' protocol (a) with slight modifications in the workup (b): (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13 and references cited therein,
  • 23
    • 33750966348 scopus 로고    scopus 로고
    • For reaction with nitroethane and transformations, see also: García Ruano, J. L.; López-Cantarero, J.; de Haro, T.; Alemán, J.; Cid, M. B. Tetrahedron 2006, 62, 12197.
    • For reaction with nitroethane and transformations, see also: García Ruano, J. L.; López-Cantarero, J.; de Haro, T.; Alemán, J.; Cid, M. B. Tetrahedron 2006, 62, 12197.
  • 24
    • 17244375162 scopus 로고    scopus 로고
    • For a review article on the conjugate additions of nitroalkanes, see
    • For a review article on the conjugate additions of nitroalkanes, see: Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.
    • (2005) Chem. Rev , vol.105 , pp. 933
    • Ballini, R.1    Bosica, G.2    Fiorini, D.3    Palmieri, A.4    Petrini, M.5
  • 25
    • 38849191443 scopus 로고    scopus 로고
    • We observed a similar behavior when the corresponding N-sulfonylnitroamine, obtained by oxidation of the corresponding N-sulfinylnitroamine 1a was subjected to Michael addition conditions.
    • We observed a similar behavior when the corresponding N-sulfonylnitroamine, obtained by oxidation of the corresponding N-sulfinylnitroamine 1a was subjected to Michael addition conditions.
  • 26
    • 38849175124 scopus 로고    scopus 로고
    • When we used nitroamine with a phenyl group (1b) as starting material, compound obtained from retro aza-Henry reaction turned out to be the main product under most of the conditions used.
    • When we used nitroamine with a phenyl group (1b) as starting material, compound obtained from retro aza-Henry reaction turned out to be the main product under most of the conditions used.
  • 27
    • 38849098708 scopus 로고    scopus 로고
    • For enantioselective Michael addition of nitro derivatives with cinchona alkaloids see for example a review article: Almaşi, D, Alonso, D. A, Nájera, C. Tetrahedron: Asymmetry 2007, 299
    • For enantioselective Michael addition of nitro derivatives with cinchona alkaloids see for example a review article: Almaşi, D.; Alonso, D. A.; Nájera, C. Tetrahedron: Asymmetry 2007, 299.
  • 29
    • 38849197227 scopus 로고    scopus 로고
    • SCX (Strong cation exchange) resin to effect catch and release purification.
    • SCX (Strong cation exchange) resin to effect "catch and release" purification.
  • 30
    • 0034710496 scopus 로고    scopus 로고
    • For another example of synthesis of piperidones from sylfinylimines, see
    • For another example of synthesis of piperidones from sylfinylimines, see: Davis, F. A.; Chao, B. Org. Lett. 2000, 17, 2623.
    • (2000) Org. Lett , vol.17 , pp. 2623
    • Davis, F.A.1    Chao, B.2
  • 31
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    • 3 and then filtered through a sort pad of silica gel eluting with EtOAc. The formation of a 87/13 mixture of 5a and 5a′ supports that epimerization is taking place under these conditions.
    • 3 and then filtered through a sort pad of silica gel eluting with EtOAc. The formation of a 87/13 mixture of 5a and 5a′ supports that epimerization is taking place under these conditions.
  • 32
    • 84985146137 scopus 로고    scopus 로고
    • A similar strategy that also uses aza-Henry reaction and cyclization has been described to obtained racemic 5-nitro-6-substituted lactames: Bhagwatheeswaran, H; Gaur, S. P, Jain, P. C. Synthesis 1976, 615
    • A similar strategy that also uses aza-Henry reaction and cyclization has been described to obtained racemic 5-nitro-6-substituted lactames: Bhagwatheeswaran, H; Gaur, S. P.; Jain, P. C. Synthesis 1976, 615.
  • 33
    • 38849129116 scopus 로고    scopus 로고
    • Although in most of the cases the amine has been previously passed through a SCX column, it has been proven that the yields of the final piperidones are similar when the reaction crudes are directly treated with NH3 in MeOH see note b in entry 2 of Table 2 and Scheme 3
    • 3 in MeOH (see note b in entry 2 of Table 2 and Scheme 3).
  • 39
    • 29544439946 scopus 로고    scopus 로고
    • For some examples of asymmetric synthesis of CP-99,994, see: (a) Xu, X.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. Eur. J. 2006, 12, 466.
    • For some examples of asymmetric synthesis of CP-99,994, see: (a) Xu, X.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. Eur. J. 2006, 12, 466.
  • 42
    • 0041302241 scopus 로고    scopus 로고
    • For Michael addition of other nitro derivatives on this substrate, see
    • For Michael addition of other nitro derivatives on this substrate, see: Miyake, N.; Kitazume, T. J. Fluorine Chem. 2003, 122, 243.
    • (2003) J. Fluorine Chem , vol.122 , pp. 243
    • Miyake, N.1    Kitazume, T.2
  • 44
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    • For a discussion of the stereochemical assignment as well as some molecular modeling supporting such assignment, see the Supporting Information
    • For a discussion of the stereochemical assignment as well as some molecular modeling supporting such assignment, see the Supporting Information.
  • 45
    • 33644784912 scopus 로고    scopus 로고
    • To prepare 7a and 7b, we followed the same procedure described for the synthesis of the corresponding t-Bu (Ellman) sulfinimine-ethanol adducts: Kuduk, S. D.; Di Marco, C. Ng.; Pitzenberger, S. M.; Tsou, N. Tetrahedron Lett. 2006, 47, 2377.
    • To prepare 7a and 7b, we followed the same procedure described for the synthesis of the corresponding t-Bu (Ellman) sulfinimine-ethanol adducts: Kuduk, S. D.; Di Marco, C. Ng.; Pitzenberger, S. M.; Tsou, N. Tetrahedron Lett. 2006, 47, 2377.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.