4796
D. Brózda et al. / Tetrahedron: Asymmetry 10 (1999) 4791–4796
N-Tosylate: crystals, m.p. 95–96.5°C (methanol); IR cm−1: 1342, 1163; 1H NMR δ: 1.5 (d, J=7.14 Hz,
3H, CH3), 2.43 (s, 3H, Ar-CH3), 3.03 (dd, J=6.3, 15.4 Hz, 1H, CH2), 3.13 (dd, J=3.8, 15.4 Hz, 1H, CH2),
3.2, 3.33, 3.62, 3.84 (4s, 3H each, OCH3), 4.27 (dd, J=3.8, 6.3, 1H, CH), 5.03 (q, J=7 Hz, 1H, CH), 6.43,
6.73, 6.74 (3s, 3H, Ar-H), 7.32 (d, J=8.5 Hz, 2H, Ar-H), 7.80 (d, J=8.2 Hz, 2H, Ar-H); MS m/z (%): 423
(M+, 4), 360 (4), 268 (16), 165 (72), 75 (100). Found: C, 59.28; H, 7.17; N, 3.38. C21H29NO6S (423.17)
requires: C, 59.60; H, 6.91; N, 3.31.
4.4.3. (4-Methoxyphenyl)-[1-(3,4-dimethoxyphenyl)ethyl]-amine 13
Crystals, m.p. 81–82°C (ether). IR cm−1: 3400, 1520; 1H NMR δ: 1.49 (d, J=6.7 Hz, 3H, CH3), 1.57
(s, 1H, NH), 3.70, 3.87, 3.89 (3s, 3H each, OCH3), 4.35 (q, J=6.7 Hz, 1H, CH), 6.49 (d, J=8.9 Hz, 2H,
Ar-H), 6.70 (d, J=8.9 Hz, 2H, Ar-H), 6.82–6.92 (m, 3H, Ar-H); MS m/z (%): 287 (M+, 77), 165 (100),
150 (11), 123 (20). Found: C, 70.87; H, 7.37; N, 4.82. C17H21NO3 (287.28) requires: C, 71.06; H, 7.37;
N, 4.87.
Acknowledgements
This work was financially supported by KBN grant no. 3 T09A 027 17.
References
1. Coppi, L.; Giordano, C.; Longoni, A.; Panossian, S. Chirality in Industry II; John Wiley & Sons: Chichester, New York,
1997; pp. 353–362.
2. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999–1004.
3. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895–1946.
4. North, M. J. Chem. Soc., Perkin Trans. 1 1998, 2959–2971.
5. Bloch, R. Chem. Rev. 1998, 98, 1407–1438.
6. Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681–6684.
7. Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1991, 32, 3095–3098.
8. Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1993, 4, 1603–1606.
9. Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429–4438.
10. Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527–2533.
11. Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705–1707.
12. Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165–168.
13. Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77–80.
14. Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron: Asymmetry 1999, 10, 221–223.
15. Jones, C. A.; Jones, I. G.; North, M.; Pool, C. R. Tetrahedron Lett. 1995, 36, 7885–7888.
16. Jones, C. A.; Jones, I. G.; Mulla, M.; North, M.; Sartori, L. J. Chem. Soc., Perkin Trans. 1 1997, 2891–2896.
17. Rozwadowska, M. D. Tetrahedron: Asymmetry 1998, 9, 1615–1618.
18. Whaley, W. M.; Meadow, M. J. Chem. Soc. 1953, 1067–1070.
19. Lejay, P; Viel, C. Ann. Chim. (Paris) 1977, 2, 87–96; [C. A. 1977, 87, 117645b].
20. Rai, M.; Kaur, B.; Dhir, B. S. J. Indian Chem. Soc. 1982, 59, 416–417.
21. Battersby, A. R.; Edwards, T. P. J. Chem. Soc. 1960, 1214–1221.
22. Bussche-Hunnefeld, C.; Beck, A. K.; Seebach, D. Helvetica Chim. Acta 1992, 75, 438–441.
23. Ponzo, V. L.; Kaufman T. S. Tetrahedron Lett. 1995, 36, 9105–9108.
24. Gant, T. G.; Meyers, A. I. Tetrahedron 1997, 50, 2297–2360.
25. Spath, E.; Dengen F. Ber. 1938, 71, 113–119.
26. Menachery, M. D.; Lavanier G. L.; Wetherly, M. L.; Guinaudeau, H.; Shamma, M. J. Nat. Prod. 1986, 49, 745–778.