Synthesis of tetracyclic heterocompounds as selective estrogen receptor modulators. Part 3. Development of an acid-catalyzed racemization process for (s)-2,8-(dimethoxy)-5-{4-[2-(1-piperidinyl)ethoxy]-phenyl}-11,12-dihydro-5H-6, 13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene

Organic Process Research and Development

Volumn 13, Issue 1, 2009, Pages 102-105

  Li, Xun ^a,b,c   Russell, Ronald K ^a,b,c   Horváth, András ^a,b,e   Jain, Nareshkumar ^a,b,d   Depré, Dominique ^a,b,e   Ormerod, Dominic ^a,b,e   Aelterman, Wim ^a,b,e   Sui, Zhihua ^a,b,d  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^c EC RED ^*  (United States)

^d EC RED   (United States)

^e JANSSEN RESEARCH FOUNDATION   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61449085676     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op800237y     Document Type: Article

References (14)

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2. (b) Kanojia, R. M.; Jain, N. F.; Ng, R.; Sui, Z.; Xu, J. WO2003053977, 2003.
3. Unpublished internal communications.
4. Uaulhier, S.; Caron, B.; Cloutier, J.; Dory, Y. L.; Favre, A.; Larouche, D.; Mailhot, J.; Quellet, C.; Schwerdtfeger, A.; Leblanc, G.; Martel, C.; Simard, J.; Merand, Y.; Belanger, A.; Labrie, C.; Labrie, F. J. Med. Chem. 1997, 40, 2117.
5. The optically pure (99.0% ee) (R)-enantiomer 3a was obtained from a preparative chiral HPLC separation of its racemate 3, which was prepared in-house and described as compound 11 in ref 1a of this publication.
6. (a) Jiang, Y. L.; Stivers, J. T. Tetrahedron Lett. 2003, 44, 4051.
7. (b) Cheng, K.; Liang, G.; Hu, C. Molecules 2008, 13, 938.
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9. (a) Stahl, P. H.; Wermuth, C. G., Eds. Handbook of Pharmaceutical Salts Properties, Selection, and Use; Wiley-VCH: Zürich, Switzerland, 2002; Vol. 28, p 75.
10. (b) Stahl, P. H.; Wermuth, C. G., Eds. Handbook of Pharmaceutical Salts Properties, Selection, and Use; Wiley-VCH: Zürich, Switzerland, 2002; Vol. 28, pp 9-290.
11. (c) Leuches, M.; Zundel, G. Can. J. Chem. 1980, 58, 311.
12. + = 514), and HPLC analytical data with an inhouse prepared authentic compound 4b.
13. (a) March, J. Advanced Organic Chemistry: Reaction, Mechanisms, and Structure, 4th ed.; John Wiley & Sons, Inc.: New York, U.S.A., 1992; Vol. 16, pp 5-174.
14. (b) Laube, T. Angew. Chem., Int. Ed. Engt. 1986, 25, 349.