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Volumn 65, Issue 19, 2000, Pages 6283-6287

Chiral mandelic acid template provides a highly practical solution for (S)-oxybutynin synthesis

Author keywords

[No Author keywords available]

Indexed keywords

MANDELIC ACID; OXYBUTYNIN;

EID: 0034703312     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo005562f     Document Type: Note
Times cited : (78)

References (49)
  • 1
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    • Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt
    • (a) Seebach, D. In Modern Synthetic Methods; Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt, 1980.
    • (1980) Modern Synthetic Methods
    • Seebach, D.1
  • 24
    • 0003129117 scopus 로고
    • Scheffold, R., Ed.; Salle+Sauerlander: Aarau
    • (b) Seebach, D.; Hungerbuhler E. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle+Sauerlander: Aarau, 1980; Vol. 2, pp 91-171.
    • (1980) Modern Synthetic Methods , vol.2 , pp. 91-171
    • Seebach, D.1    Hungerbuhler, E.2
  • 27
    • 0343778312 scopus 로고
    • 2CCHO were also examined. However, the diastereoselectivity in the preparation of these dioxolones was poor
    • 2CCHO were also examined. However, the diastereoselectivity in the preparation of these dioxolones was poor.
    • (1984) Tetrahedron , pp. 40
    • Seebach, D.1    Naef, R.2    Calderari, G.3
  • 29
    • 0042552592 scopus 로고
    • (b) Polonski, T. Tetrahedron 1983, 39, 3131. Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1881.
    • (1983) Tetrahedron , vol.39 , pp. 3131
    • Polonski, T.1
  • 33
    • 0342473207 scopus 로고    scopus 로고
    • note
    • 4 provided reasonable selectivities from 90:10 to 94:6. matrix presented
  • 34
    • 0343342665 scopus 로고    scopus 로고
    • Using 1.1 equiv of pivaldehyde is ideal for the reaction. Using more equivalents of aldehyde results in formation of the trimer byproduct 10; see Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1998, 120, 984.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 984
    • Denmark, S.E.1    Wilson, T.2    Willson, T.M.3
  • 35
    • 0342473210 scopus 로고    scopus 로고
    • note
    • 5 according to Scheme 3, path a.
  • 36
    • 0342907570 scopus 로고    scopus 로고
    • The reaction was performed at -100 °C; however the rate of reaction was greatly reduced and the selectivity was not improved
    • The reaction was performed at -100 °C; however the rate of reaction was greatly reduced and the selectivity was not improved.
  • 37
    • 0342907571 scopus 로고    scopus 로고
    • Heating to higher temperatures (>0 °C) results in some decomposition
    • Heating to higher temperatures (>0 °C) results in some decomposition.
  • 47
    • 0342473209 scopus 로고    scopus 로고
    • note
    • (a) To obtain a clean reaction product, the order of addition of thionyl chloride and pyridine is essential. Thionyl chloride is added first, followed by pyridine. (b) A mild wash with aqueous ammonium chloride is necessary to remove sulfur impurities, which can poison Pd/C and render the hydrogenation to (S)-1 ineffective.
  • 48
    • 0342907569 scopus 로고    scopus 로고
    • note
    • Alkylation of (S,S)-2 with cyclohexyl iodide was unsuccessful. The more expensive 3-bromocyclohexene undergoes smooth alkylation to provide the alkylated adduct in 77% yield with >98:2 selectivity, which after hydrogenation followed by hydrolysis provides (S)-1 in 97% ee in high yields. This alkylation chemistry is a facile entry to (S)-1. However, the availability of the bromocyclohexenyl in large scale limits practicality. matrix presented
  • 49
    • 0343778302 scopus 로고    scopus 로고
    • The stereochemical assignments of 7, 8, and 9, respectively, were predicated in an analogus manner to the (S)-1 as discussed in ref 12b
    • The stereochemical assignments of 7, 8, and 9, respectively, were predicated in an analogus manner to the (S)-1 as discussed in ref 12b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.