Facile preparation of cyclopropylamines from carboxamides

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1584-1585

  Lee, Jinhwa ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; CYCLOPROPYLAMINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030894464     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962368d     Document Type: Article

References (24)

1. (a) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291.
2. (b) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
3. (c) Lee, J.; Kim, Y. G.; Bae, J.; Cha, J. K. J. Org. Chem. 1996, 61, 4878.
4. See also: (d) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
5. (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
6. (b) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294.
7. (c) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234.
8. (d) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428.
9. (e) Kulinkovich, O. G.; Sorokin, V. L.; Kel'in, A. V. Zh. Org. Khim. 1993, 29, 66.
10. (f) Kulinkovich, O. G.; Savchenko, A. I.; Sviridov, S. V.; Vasilevskii, D. A. Mendeleev Commun. 1993, 192.
11. (a) de Meijere, A.; Kozhushkov, S. I.; Spaeth, T.; Zefirov, N. S. J. Org. Chem. 1993, 58, 502,
12. (b) Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413.
13. See also: (a) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079. (c) Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849 and references cited therein.
14. See also: (a) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079. (c) Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849 and references cited therein.
15. See also: (a) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079. (c) Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849 and references cited therein.
16. Only a few general methods have previously been developed for the preparation of substituted cyclopropylamines: Vilsmaier, E. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, 1987; Chapter 22.
17. f value of the major isomer of 1c in 7:1 hexane-EtOAc is 0.73, while that of the minor isomer is only 0.35.
18. Cf. (a) Seebach, D.; Schiess, M. Helv. Chim. Acta 1982, 65, 2598. (b) Seebach, D.; Beck, A. K.; Schiess, M.; Widler, L.; Wonnacott, A. Pure Appl. Chem. 1983, 55, 1807. (c) Bertschart, C.; Seebach, D. Helv. Chim. Acta 1987, 70, 2215.
19. Cf. (a) Seebach, D.; Schiess, M. Helv. Chim. Acta 1982, 65, 2598. (b) Seebach, D.; Beck, A. K.; Schiess, M.; Widler, L.; Wonnacott, A. Pure Appl. Chem. 1983, 55, 1807. (c) Bertschart, C.; Seebach, D. Helv. Chim. Acta 1987, 70, 2215.
20. Cf. (a) Seebach, D.; Schiess, M. Helv. Chim. Acta 1982, 65, 2598. (b) Seebach, D.; Beck, A. K.; Schiess, M.; Widler, L.; Wonnacott, A. Pure Appl. Chem. 1983, 55, 1807. (c) Bertschart, C.; Seebach, D. Helv. Chim. Acta 1987, 70, 2215.
21. 4 to convert 7 to the corresponding alcohol so as to facilitate separation from 1b. (b) Diastereoselectivity was measured by GC.
22. 3b In our hands, however, the reaction of 2e with ethyl or hexyl Grignard reagents, reported to require heating, readily took place at room temperature in comparable yields. In any event, we believe that the postulated intermediate 4 has only a transient lifetime.
23. (a) In contrast to amides 2a-d, 2e-i gave none of the ketones derived from hydrolysis of 5 or 6. (b) None of the methyl-branched ketone, the hydrolysis product of the intermediate 6, was detected in any of the interception experiments with amide 2a-i. These results do not necessarily exclude the intermediacy of 6, but rather its transient nature may have precluded the detection.
24. In our previous paper, (ref 1 and see also ref 4a), we had favored selective insertion of the ester carbonyl group between Ti and the more substituted carbon on the basis of the reductive dimerization product of the starting olefin. However, it is noteworthy that, in the case of zirconocene-alkene complexes, the coupling with aldehydes is known to take place with the opposite orientation to that with alkenes: Takahashi, T.; Suzuki, N.; Hasegawa, M.; Nitto, Y.; Aoyagi, K.; Saburi, M. Chem. Lett. 1992, 331.