Optical resolution, stereoselective synthesis, and crystal structure of 9α-(3-azabicyclo[3,3,1]nonanyl)-2′cyclopentyl-2′-hydroxy- 2′-phenylacetate

Synthetic Communications

Volumn 35, Issue 10, 2005, Pages 1403-1412

  Liu, Yan Qing ^b   Liu, He ^a   Zhong, Bo Hua ^a   Deng, Yu Lin ^b   Liu, Ke Liang ^a  

^a BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

^b BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Crystal structure; Optical resolution; Stereoselective synthesis

Indexed keywords

9ALPHA (3 AZABICYCLO[3,3,1]NONANYL) 2' CYCLOPENTYL 2' HYDROXY 2' PHENYLACETATE; BENZALDEHYDE; MANDELIC ACID; PHENYLACETIC ACID DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TOLUENESULFONYLGLUTAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; OPTICAL RESOLUTION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 19544389342     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200057293     Document Type: Article

References (24)

1. (a) Caner, H.; Groner, E.; Lery, L.; Agranat, I. Trends in the development of chiral drugs. Drug Discovery Today 2004, 9, 105;
2. (b) Rouhi, A. M. Chiral business. Chem. Eng. News 2003, 81, 45.
3. Food and Drug Administration, FDA's policy statement for the development of new stereoisomeric drugs. Fed. Reg. 22 249, 1992, 57.
4. (a) Liu, H.; Liu, C. H.; Han, X. Y.; Zhong, B. H.; Liu, K. L. Studies on crystal structure of inclusion chiral crystal of (S)-α-cyclopentyl- α-hydroxy-α-thienylacetic acid with (R)-α-methyl benylamine. J. Chem. Res. 2004, 482;
5. (b) Liu, H.; Han, X. Y.; Liu, C. H.; Zhong, B. H.; Liu, K. L. Crystal structure of (2S,5R)-2-(tert-butyl)5-phenyl-5-(cyclopentyl-ol)-1,3-dioxolan-4- one. Anal. Sci. 2004, 20, x121;
6. (c) Wu, P. J.; Yun, L. H. Synthesis of anticholinergics of 2-(1-naphtyl)-2-cyclopentyl-2-hydroxy ethoxy cyclic amine compounds. Chin. J. Med. Chem. 1999, 9, 102.
7. Wang, L.; Yun, L. H.; Zhang, Q. K. Synthesis of optical isomers of 2α-(2′,2′disubstitiuted-2′-hydroxyethoxy)tropane as potential M-receptor antagonists. Acta. Pharmaceutica Sin. 1996, 31, 790.
8. 3 receptor antagonist. Tetrahedron 2000, 56, 9901;
9. (b) McPherson, D. W.; Knapp, F. F. Structure elucidation via stereoselective synthesis of the acetate center of 1-azabicyclo[2.2.2]oct-3-yl α-hydroxy-α-(1-iodo-1-propen-3-yl)-α-phenylacetate (IQNP). A high affinity muscarinic imaging agent for SPECT. J. Org. Chem. 1996, 61, 8335;
10. (c) Carter, J. P.; Noronha-Blob, L.; Audia, V. H.; Dupout, A. C.; McPherson, D. W.; Natalie, K. J.; Rzeszotarski, J.; Spagnuolo, C. J.; Wald, P. P.; Kaiser, C. Analogues of oxybutynin, Synthesis and antimuscarinic and bladder activity of some substituted7-amino-1-hydroxy-5-heptyn-2-ones and related compounds. J. Med. Chem. 1993, 4, 2183.
11. Kozma, D.; Ács, M.; Fogassy, E. Predictions of which diastereoisomeric salt precipitates during an optical resolution via diastereoisomeric salt formation, Tetrahedron 1994, 50, 6907.
12. Vries, T.; Wynberg, H.; van Echtenm, E.; Koek, J.; ten Hoeve,W.; Kellogg,R. M.: Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. The family approach to the resolution of racemates. Angew. Chem., Int. Ed. Engl. 1998, 37, 2349.
13. 1A affinity. Bioorg. Med. Chem. Lett. 2004, 14, 5281.
14. (a) Grover, P. T.; Bhongle, N. N.; Wald, S. A.; Senanayake, C. H. Chiral mandelic acid template provides a highly practical solution for (S)-oxybutynin synthesis. J. Org. Chem. 2000, 65, 6283;
15. (b) Ortholand, J. Y.; Vicart, N.; Greiner, A. Transacetalization reaction of acetals by lactic acid. Diastereoselective synthesis of 2-substituted 5-methyl-1,3-dioxolan-4-ones. J. Org. Chem. 1995, 60, 1880;
16. (c) Seebach, D.; Naef, R.; Calderari, G. α-Alkylation of α-heterosubstituted carboxylic acids with racemization. Tetrahedron 1984, 40, 1313;
17. (d) Seebach, D.; Naef, R. 274, Enantioselective generation and diastereoselective reactions of chiral enolates derived from α-heterosubstituted carboxylic acids. Helv. Chim. Acta 1981, 64, 2704.
18. 3 receptor antagonist, J-104129. Bioorg. Med. Chem. Lett. 1999, 9, 2037.
19. Gupta, P.; Fernandes, R. A.; Kumar, P. An asymmetric dihydroxylation route to (S)-oxybutynin. Tetrahedron Lett. 2003, 44, 4231.
20. (a) Kunaran, D.; Ponnuswamy, M. N.; Shanmugam, G.; Ponnuswamy, S.; Jevaraman, R.; Shivakuman, K.; Fun, H.-K. Molecular structure and conformation of three 3-azabicyclonane. Acta. Cryst. 1999, B55, 793L;
21. (b) Vijayalakshmi, L.; Parthasarathi, V.; Venkatraj, M.; Jeyaraman, R. 2,4-Bis(O-tolyl)-3-azabicyclo[3.3.1]nonan-9-one. Acta. Cryst. 2000, C56, 1240.
22. (a) Desiraju, G. R. The C-H⋯O hydrogen bond in crystals: What is it? Acc. Chem. Res. 1991, 24, 290;
23. (b) Jeffrey, G. A.; Saenger, W. Eds.; Hydrogen Bonding in Biological Structurerey; Springer: Berlin, 1991; pp. 29-32.
24. Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution; Göttingen University: Germany, 1997.