Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks

Tetrahedron

Volumn 64, Issue 10, 2008, Pages 2456-2464

  Gijsen, Harrie J M ^a   De Cleyn, Michel J A ^a   Love, Christopher J ^a   Surkyn, Michel ^a   Van Brandt, Sven F A ^a   Verdonck, Marc G C ^a   Moens, Luc ^a   Cuypers, Jef ^a   Bosmans, Jean Paul R M A ^a  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOMETHYLPIPERIDIN 3 OL DERIVATIVE; ACETOCYANOHYDRIN; LITHIUM DERIVATIVE; N BENZYL 3,4 EPOXYPIPERIDINE; NITRILE; NITROGEN 13; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROBORATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 38649100623     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.12.055     Document Type: Article

References (29)

1. De Maeyer J.H., Prins N.H., Schuurkes J.A.J., and Levebvre R.A. J. Pharmacol. Exp. Ther. 317 (2006) 955-964
2. Buffat M.G.P. Tetrahedron 60 (2004) 1701-1729
3. Weintraub P.M., Sabol J.S., Kane J.M., and Borcherding D.R. Tetrahedron 59 (2003) 2953-2989 and references cited in these reviews
4. Sonda S., Kawahara T., Ktayama K., Sato N., and Asano K. Bioorg. Med. Chem. 13 (2005) 3295-3308
5. For example:
6. Efange S.M.N., Khare A.B., Foulon C., Akella S.K., and Parsons S.M. J. Med. Chem. 37 (1994) 2574-2582
7. Naito T., Nakagawa K., Nakamura T., Kasei A., Ninomiya I., and Kiguchi T. J. Org. Chem. 64 (1999) 2003-2009
8. Langlois N., and Calvez O. Synth. Commun. 28 (1998) 4471-4478
9. Marquis R.W., Yamashita D.S., Ru Y., LoCastro S.M., Oh H.-J., Erhard K.F., DesJarlais R.L., Head M.S., Smith W.W., Zhao B., Janson C.A., Abdel-Mgeguid S.S., Tomaszed T.A., Levy M.A., and Veber D.F. J. Med. Chem. 41 (1998) 3563-3567
10. Kubota D., Ishikawa M., Ishikawa M., Yahata N., Murakami S., Fujishima K., Kitakaze M., and Ajito K. Bioorg. Med. Chem. 14 (2006) 4158-4181
11. Lewis N.J., Barker K.K., Fox R.M., and Mertes M.P. J. Med. Chem. 16 (1973) 156-159
12. Furegati S., Ganci W., Gorla F., Ringeisen U., and Rueedi P. Helv. Chim. Acta 87 (2004) 2629-2661
13. Petrow V., and Stephenson O. J. Pharm. Pharmacol. 14 (1962) 306-314
14. Moriconi E.J., and Misner R.E. J. Org. Chem. 34 (1969) 3672-3674
15. Brown H.C. Hydroboration (1962), W.A. Benjamin, New York, NY
16. Kergomard A., and Veschambre H. Tetrahedron Lett. 17 (1976) 4069-4072
17. Golodova K.G., and Yakimovitch S.I. Zh. Org. Khim. 8 (1972) 2481-2489
18. Takemura S., Miki Y., Uono M.i., Yoshimura K., Kuroda M., and Suzuki A. Chem. Pharm. Bull. 29 (1981) 3026-3032
19. Imanishi T., Shin H., Hanaoka M., Momose T., and Imanishi I. Chem. Pharm. Bull. 30 (1982) 3617-3623
20. Ciaccio J.A., Stanescu C., and Bontemps J. Tetrahedron Lett. 33 (1992) 1431-1434
21. Livinghouse T. Org. Synth. Coll. 7 (1990) 517-522
22. Recently, the epoxidation of 17 to 24, using similar conditions as described here, was published:. Grishina G.V., Borisenko A.A., Veselov I.S., and Petrenko A.M. Russ. J. Org. Chem. 41 (2005) 272-278
23. Ciaccio J.A., Smrtka M., Maio W.A., and Rucando D. Tetrahedron Lett. 45 (2004) 7201-7204
24. Bosmans, J.-.P. R. M. A.; De Cleyn, M. A. J.; Surkyn, M. PCT Int. Appl. WO199902156, 1999;
25. Chem. Abstr. 130 (1999) 139258
26. Bosmans, J.-.P. R. M. A.; Gijsen, H. J. M.; Mevellec, L. A. PCT Int. Appl. WO2005000838, 2005;
27. Chem. Abstr. 142 (2005) 114101
28. Laduron F., Tamborowski V., Moens L., Horvath A., De Smaele D., and Leurs S. Org. Process Res. Dev. 9 (2005) 102-104
29. D +4.4 (c 0.5, MeOH), with further analytical data in agreement with the racemic 14.