Efficient enantioselective formal synthesis of Ro 67-8867, a NMDA 2B receptor antagonist

Synlett

Volumn , Issue 7, 2005, Pages 1170-1172

  Déchamps, Ingrid ^a   Pardo, Domingo Gomez ^a   Karoyan, Phillipe ^b   Cossy, Janine ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Amino zinc ene enolate cyclization; Asymmetric synthesis; Piperidines; Prolinol; Ring expansion

Indexed keywords

AMINE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2B; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PIPERIDINE DERIVATIVE; PROLINE DERIVATIVE; RO 678867; SULFONE; UNCLASSIFIED DRUG; ZINC;

ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CONFERENCE PAPER; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; HYDROGENOLYSIS; OPTICAL ROTATION; REPRODUCIBILITY; TECHNIQUE;

EID: 18744366995     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865225     Document Type: Conference Paper

References (34)

1. (a.) Grauert, M.; Bechtel, W. D.; Ensinger, H. A.; Merz, H.; Carter, A. J. J. Med. Chem. 1997, 40, 2922.
2. (b) Guzikowski, A. P.; Whittemore, E. R.; Woodward, R. M.; Weber, E.; Keana, J. F. W. J. Med. Chem. 1997, 40, 2424.
3. (c) Gee, K. R.; Niu, L.; Schaper, K.; Jayaraman, V.; Hess, G. Biochemistry 1999, 38, 3140.
4. (a) Alanine, A.; Burner, S.; Buettelmann, B.; Heitz Neidhart, M.-P.; Jaeschke, G.; Pinard, E.; Wyler, R. WO 0075109, 2000; Chem. Abstr. 2000, 134, 42064.
5. (b) Crameri, Y.; Scalone, M.; Waldmeier, P.; Widmer, U. EP 1136475, 2001; Chem. Abstr. 2001, 135, 272882.
6. (c) Alanine, A.; Buettelmann, B.; Fisher, H.; Huwyler, J.; Heitz Neidhart, M.-P.; Jaeschke, G.; Pinard, E.; Wyler, R. WO 0216321, 2002; Chem. Abstr. 2002, 136, 216649.
7. (d) Scalone, M.; Waldmeier, P. Org. Process Res. Dev. 2003, 7, 418.
8. (a) Karoyan, P.; Chassaing, G. Tetrahedron Lett. 1997, 38, 85.
9. (b) Lorthiois, E.; Marek, I.; Normant, J. Tetrahedron Lett. 1997, 38, 89.
10. (c) Karoyan, P.; Chassaing, G. Tetrahedron: Asymmetry 1997, 8, 2025.
11. (d) Lorthiois, E.; Marek, I.; Normant, J. J. Org. Chem. 1998, 63, 2442.
12. (e) Karoyan, P.; Chassaing, G. Tetrahedron Lett. 2002, 43, 253.
13. (f) Karoyan, P.; Chassaing, G. Tetrahedron Lett. 2002, 43, 1221.
14. (g) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256.
15. (h) Quancard, J.; Magellan, H.; Lavielle, S.; Chassaing, G.; Karoyan, P. Tetrahedron Lett. 2004, 45, 2185.
16. (i) Quancard, J.; Labonne, A.; Jacquot, Y.; Chassaing, G.; Lavielle, S.; Karoyan, P. J. Org. Chem. 2004, 69, 7940.
17. For comprehensive reviews, see: (a) Cossy, J.; Gomez Pardo, D. Chemtracts 2002, 15, 579.
18. (b) Cossy, J.; Gomez Pardo, D. Targets in Heterocyclic Systems 2002, 6, 1.
19. +], 265 (23), 264 (100), 143 (4), 106 (5), 105 (56), 104 (3), 103 (6), 91 (19), 79 (7), 77 (6), 68 (5).
20. 1H NMR and GC-MS.
21. +], 280 (5), 265 (22), 264 (100), 161 (8), 160 (66), 143 (6), 106 (8), 105 (79), 103(8), 91 (27), 79 (10), 77 (9), 68 (7).
22. (a) Cossy, J.; Dumas, C.; Michel, P.; Gomez Pardo, D. Tetrahedron Lett. 1995, 36, 549.
23. (b) Cossy, J.; Dumas, C.; Gomez Pardo, D. Synlett 1997, 905.
24. (c) Cossy, J.; Dumas, C.; Gomez Pardo, D. Bioorg. Med. Chem. Lett. 1997, 7, 1343.
25. (d) Wilken, J.; Kossenjans, M.; Saak, W.; Haase, D.; Pohl, S.; Martens, J. Liebigs Ann: 1997, 573.
26. (e) Langlois, N.; Calvez, O. Synth. Commun. 1998, 28, 4471.
27. (f) Davis, P. W.; Osgood, S. A.; Hébert, N.; Sprankle, K. G.; Swayze, E. E. Biotechnol. Bioeng. 1999, 61, 143.
28. (g) Cossy, J.; Dumas, C.; Gomez Pardo, D. Eur. J. Org. Chem. 1999, 1693.
29. (h) Michel, P.; Rassat, A. J. Org. Chem. 2000, 65, 2572.
30. (i) Cossy, J.; Mirguet, O.; Gomez Pardo, D. Synlett 2001, 1575.
31. (j) Brandi, A.; Cicchi, S.; Paschetta, V.; Gomez Pardo, D.; Cossy, J. Tetrahedron Lett. 2002, 43, 9357.
32. (k) Deyine, A.; Delcroix, J.-M.; Langlois, N. Heterocycles 2004, 64, 207.
33. +], 281 (23), 280 (100), 218 (14), 190(6), 105 (32), 103 (4), 91 (18). 79 (5), 77 (5).
34. +], 162 (9), 147 (8), 131 (7), 118 (32), 115 (13), 100 (20), 92 (11), 91 (67), 82 (22), 77 (11), 72 (11), 71 (42),