2458
B. B. Snider, S. M. O’Hare / Tetrahedron Letters 42 (2001) 2455–2458
gare, J. A. Tetrahedron Lett. 1998, 39, 2663–2666; (l)
120.9, 116.6, 65.7, 53.2, 51.8, 46.1, 40.5, 36.5, 25.81,
25.71, 18.0 (four quaternary carbons were not observed);
HRMS (DCI, NH3) calcd for C19H26N3O3 (MH+)
Kim, H.-O.; Mathew, F.; Ogbu, C. Synlett 1999, 193–
194; (m) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamil-
ton, A. D. J. Org. Chem. 2000, 65, 1566–1568.
1
344.1974, found 344.1977. 21: H NMR (D2O, HDO at
7. (a) von Braun, J. Chem. Ber. 1909, 42, 2035–2057; (b)
Short, J. H.; Biermacher, U.; Dunnigan, D. A.; Leth, T.
D. J. Med. Chem. 1963, 6, 275–283.
4.79, 500 MHz): 7.93 (d, 1, J=1.0), 7.75 (dd, 1, J=8.5,
1.0), 6.91 (d, 1, J=8.5), 5.37 (br t, 1, J=7), 5.32 (d, 1,
J=6.9), 4.40 (dd, 1, J=12.2, 2.4), 4.36 (dd, 1, J=12.2,
2.0), 3.99 (dd, 1, J=15.2, 7), 3.96 (dd, 1, J=15.2, 7),
3.63–3.45 (m, 2), 2.85–2.77 (m, 1), 2.30–2.22 (m, 1),
2.16–2.05 (m, 1), 1.79 (s, 3), 1.75 (s, 3); 13C NMR: 157.8,
154.8, 131.4, 131.2, 120.6, 120.1, 117.7, 117.5, 65.1, 54.4,
46.6, 40.1, 36.2, 24.9, 23.9, 17.3 (2 quaternary carbons
were not observed); HRMS (FAB, DMSO/NBA) calcd
for C18H24N3O3 (MH+) 330.1818, found 330.1818.
9. Jordis, U.; Grohmann, F.; Ku¨enburg, B. Org. Prep.
Proced. Int. 1997, 29, 549–560.
1
8. 4b: H NMR: 7.38 (dd, 2, J=7.2, 7.2), 7.33–7.29 (m, 3),
4.66 (dd, 1, J=7.3, 7.3), 3.72 (ddd, 1, J=7.2, 7.2, 6.8),
3.62–3.57 (m, 1), 2.38–2.30 (m, 1), 2.10–1.95 (m, 2),
1.92–1.83 (m, 1); 13C NMR: 139.7, 128.8 (2 C), 128.2,
126.3 (2 C), 116.9, 65.9, 51.4, 35.5, 24.8; IR 2211. 6bb: 1H
NMR: 7.35–7.31 (m, 2), 7.27–7.23 (m, 3), 5.07 (br t, 1,
J=6.7), 4.75 (dd, 1, J=7.9, 3.2), 3.68–3.55 (m, 2), 3.61
(br d, 2, J=6.7), 2.40–2.31 (m, 1), 2.00–1.81 (m, 3), 1.64
(s, 3), 1.52 (s, 3); 13C NMR: 157.9, 144.0, 135.4, 128.7 (2
C), 127.2, 125.6 (2 C), 121.2, 61.2, 47.8, 40.2, 36.3, 25.5,
22.9, 17.7; IR 1591; HRMS (DEI) calcd for C16H23N3
10. Girault-Vexlearschi, G. Bull. Soc. Chim. Fr. 1956, 589–
606.
11. Witteveen, A. J.; Trompen, W. P.; Hackmann, J. T. Recl.
Trav. Chim. Pays-Bas 1970, 89, 121–128.
1
(M+) 257.1892, found 257.1889. 18: mp 77.5–78.5°C; H
NMR: 8.09 (s, 1), 7.84 (br d, 1, J=8.5), 6.90 (d, 1,
J=8.5), 4.16 (dd, 1, J=11, 4.3), 4.00 (d, 1, J=6.1), 3.87
(s, 3), 3.64 (dd, 1, J=11.0, 11.0), 3.10 (ddd, 1, J=10, 9,
5), 2.97 (ddd, 1, J=9, 9, 9), 2.56–2.47 (m, 1), 2.19–2.07
(m, 1), 2.07 (s, 1, NH), 1.58–1.50 (m, 1); 13C NMR:
166.8, 158.9, 132.8, 130.1, 123.3, 122.9, 117.0, 66.7, 55.6,
12. (a) Confolone, P. N.; Huie, E. M. J. Am. Chem. Soc.
1984, 106, 7175–7178; (b) Kanemasa, S.; Sakamoto, K.;
Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960–1968; (c)
Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.;
Chiarini, A.; Hucho, F.; Krogsgaard-Larsen, P.; Mellor,
I. R.; Minarini, A.; Tumiatti, V.; Usherwood, P. N. R.;
Melchiorre, C. J. Med. Chem. 1999, 42, 5212–5223.
13. (a) Lee, J. L.; Lee, H. S.; Kim, B. H. Synth. Commun.
1996, 26, 3201–3215; (b) Campi, E. M.; Jackson, W. R.;
McCubbin, Q. J.; Trnacek, A. E. Aust. J. Chem. 1996, 49,
219–230.
14. (a) Roush, W. R.; Coffey, D. S. J. Org. Chem. 1995, 60,
4412–4418; (b) Rosen, M. D.; Doubleday, M. D.; Suto,
M. J. Synth. Commun. 1998, 28, 3491–3502.
15. A column of Dowex 550A resin was pretreated with 20
volumes of 20% NaOH followed by 5 volumes of H2O
and 5 volumes of MeOH. The resin was dried under a
flow of air for 1 h.
1
51.8, 44.9, 35.4, 27.9; IR 1714. 19: H NMR: 8.16 (d, 1,
J=2.4), 7.95 (dd, 1, J=8.5, 2.4), 6.94 (d, 1, J=8.5), 4.55
(d, 1, J=6.1), 4.20 (dd, 1, J=11.0, 4.2), 3.89 (s, 3), 3.85
(dd, 1, J=11.0, 9.8), 3.57 (apparent t, 2, J=6.7), 2.72–
2.62 (m, 1), 2.32–2.23 (m, 1), 1.95–1.87 (m, 1); 13C NMR:
166.3, 158.0, 132.9, 131.8, 123.5, 118.4, 117.3, 116.4, 65.1,
1
57.5, 52.1, 48.5, 35.3, 26.0; IR 2208, 1714. 20: H NMR:
8.50 (br s, 1, J=8.5), 7.80 (dd, 1, J=8.5, 1.8), 6.79 (d, 1,
J=8.5), 5.49 (d, 1, J=7.3), 5.30 (br t, 1, J=6.7), 4.29
(dd, 1, J=11.6, 2.4), 4.24 (dd, 1, J=11.6, 2.4), 3.89 (s, 3),
3.77 (d, 2, J=6.7), 3.43 (ddd, 1, J=8.5, 8.5, 8.5), 3.36–
3.31 (m, 1), 2.62–2.55 (m, 1), 2.14–2.07 (m, 2), 1.76 (s, 3),
1.73 (s, 3); 13C NMR: 166.9, 157.5, 132.9, 129.9, 123.4,
.
.