(S)-1-aminoindane: Synthesis by chirality transfer using (R)-phenylglycine amide as chiral auxiliary

Tetrahedron Asymmetry

Volumn 14, Issue 22, 2003, Pages 3479-3485

  Uiterweerd, Patrick G H ^a   Van Der Sluis, Marcel ^a   Kaptein, Bernard ^b   De Lange, Ben ^b   Kellogg, Richard M ^a   Broxterman, Quirinus B ^b  

^a Syncom BV   (Netherlands)

^b DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOINDAN; AMIDE; IMINE; INDAN DERIVATIVE; INDANONE DERIVATIVE; METAL; PHENYLGLYCINAMIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIASTEREOISOMER; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; REDUCTION KINETICS; TRANSAMINATION;

EID: 0242541908     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.040     Document Type: Article

References (30)

1. Bruggink A., Roos E., de Vroom E. Org. Process Res. Dev. 2:1998;128-133.
2. Boesten W.H.J., Seerden J.-P.G., de Lange B., Dielemans H.J.A., Elsenberg H.L.M., Kaptein B., Moody H.M., Kellogg R.M., Broxterman Q.B. Org. Lett. 3:2001;1121-1124 Boesten, W. H. J.; Seerden, J.-P. G.; de Lange, B.; van der Sluis, M.; Kaptein, B.; Moody, H. M.; Kellogg, R. M.; Broxterman, Q. B. PCT Int. Appl, WO 01 42,173, 2001.
3. Van der Sluis M., Dalmolen J., de Lange B., Kaptein B., Kellogg R.M., Broxterman Q.B. Org. Lett. 3:2001;3943-3946.
4. Using (S)-PGA as the chiral auxiliary would yield (R)-1-aminoindane.
5. Graul A., Castaner J. Drugs of the Future. 23:1998;903-905.
6. Singh T., Stein R.G., Hoops J.F., Biel J.H., Hoya W.K., Cruz D.R. J. Med. Chem. 14:1971;283-286.
7. Sterling J., Herzig Y., Goren T., Finkelstein N., Lerner D., Goldenberg W., Miskolczi I., Molnar S., Rantal F., Tamas T., Toth G., Zagyva A., Zekany A., Lavian G., Gross A., Friedman R., Razin M., Huang W., Krais B., Chorev M., Youdim M.B., Weinstock M. J. Med. Chem. 45:2002;5260-5279.
8. Regan J., Breitfelder S., Cirillo P., Gilmore T., Graham A.G., Hickey E., Klaus B., Madwed J., Moriak M., Moss N., Pargellis C., Pav S., Proto A., Swinamer A., Tong L., Torcellini C. J. Med. Chem. 45:2002;2994-3008.
9. Yao W., Wasserman Z.R., Chao M., Reddy G., Shi E., Liu R.-Q., Covington M.B., Arner E.C., Pratta M.A., Tortorella M., Magolda R.L., Newton R., Qian M., Ribadeneira M.D., Christ D., Wexler R.R., Decicco C.P. J. Med. Chem. 44:2001;3347-3350.
10. Bøgesø K.P., Arnt J., Boeck V., Christensen A.V., Hyttel J., Gundertofte Jensen K. J. Med. Chem. 31:1988;2247-2256.
11. Lidor, R.; Bahar, E. W. O. Patent 96/21640, 1996.
12. Lidor R., Bahar E., Zairi O., Atili G., Amster D. Org. Prep. Proced. Int. 29:1997;701-706.
13. Gutman, A. L.; Zaltzman, I.; Ponomarev, V.; Sotrihin, M.; Nisnevich, G. W. O. Patent 02/068376 A1, 2002.
14. Gutman A.L., Meyer E., Kalerin E., Polyak F., Sterling J. Biotechnol. Bioeng. 40:1992;760-767.
15. Gutman A.L., Shkolnik E., Meyer E., Polyak F., Brenner D., Boltanski A. Annals New York Acad. Sci. 799:1996;620-632.
16. For other enzymatic approaches, see: (a) Stirling, D. I.; Matcham, G. W. ; Zeitlin, A. L. US Patent 5,300,437, 1994; (b) Shin, J.-S.; Kim, B.-G.; Shin, D.-H. Enzyme Microbial Technol. 2001, 29, 232-239; (c) Laumen, K.; Brunella, A. ; Graf, M.; Kittelmann, M.; Walser, P.; Ghisalba, O. Pharmacochem. Lib. 1998, 29, 17-28.
17. For other enzymatic approaches, see: (a) Stirling, D. I.; Matcham, G. W. ; Zeitlin, A. L. US Patent 5,300,437, 1994; (b) Shin, J.-S.; Kim, B.-G.; Shin, D.-H. Enzyme Microbial Technol. 2001, 29, 232-239; (c) Laumen, K.; Brunella, A. ; Graf, M.; Kittelmann, M.; Walser, P.; Ghisalba, O. Pharmacochem. Lib. 1998, 29, 17-28.
18. For other enzymatic approaches, see: (a) Stirling, D. I.; Matcham, G. W. ; Zeitlin, A. L. US Patent 5,300,437, 1994; (b) Shin, J.-S.; Kim, B.-G.; Shin, D.-H. Enzyme Microbial Technol. 2001, 29, 232-239; (c) Laumen, K.; Brunella, A. ; Graf, M.; Kittelmann, M.; Walser, P.; Ghisalba, O. Pharmacochem. Lib. 1998, 29, 17-28.
19. Brunner H., Becker R., Gauder S. Organometallics. 5:1986;739-746.
20. Takei I., Nishibayashi Y., Ishii Y., Mizobe Y., Uemura S., Hidai M. Chem. Commun. 2001;2360-2361.
21. Fernandez E., Hooper M.W., Knight F.I., Brown J.M. Chem. Commun. 1997;173-174.
22. Fernandez E., Maeda K., Hooper M.W., Brown J.M. Chem. Eur. J. 6:2000;1840-1846.
23. Gutman A.L., Etinger M., Nisnevich G., Polyak F. Tetrahedron: Asymmetry. 9:1998;4369-4379.
24. For a review on the application of (R)- and (S)-phenylethylamine as chiral auxiliary, see: Juaristi E., Léon-Romo J.L., Reyes A., Escalante J. Tetrahedron: Asymmetry. 24:1999;2441-2495.
25. Stalker R.A., Munsch T.E., Tran J.D., Nie X., Warmuth R., Beatty A., Aakeröy C.B. Tetrahedron. 58:2002;4837-4849.
26. 4 in EtOH afforded (R,S)-2 in 79% isolated yield but in only 16% de.
27. For a review on the power of High Throughput Experimentation (HTE) in Homogeneous Catalysis Research for Fine Chemicals, see: de Vries J.G., de Vries A.H.M. Eur. J. Org. Chem. 2003;799-811.
28. The catalyst loading is defined as the weight percentage of catalyst in relation to the amount of substrate.
29. 1H NMR spectral analysis in addition to their HPLC analyses. A good correlation was observed.
30. -1.