3660
D. J. Schauer, P. Helquist
PAPER
(E)-3-(4-Methoxyphenyl)-N-methylacrylamide (5c)
Using the procedure described above, 5c was isolated (yield; 42%;
42 mg) as a white crystalline solid; mp 118-122 °C; Rf = 0.06 (hex-
anes–EtOAc, 7:3).
1H NMR (500 MHz, CDCl3): d = 6.81 (dd, J = 7.0, 15.5 Hz, 1 H),
5.71 (dd, J = 1.0, 15.5 Hz, 1 H), 5.45 (br s, 1 H), 2.88 (d, J = 5.0 Hz,
3 H), 2.44 (m, 1 H), 1.06 (d, J = 6.5 Hz, 6 H).
13C NMR (125 MHz, CDCl3): d = 167.2, 151.1, 120.8, 30.9, 26.5,
21.7.
IR (film): 3272, 3098, 2932, 1655, 1605, 1572, 1510, 1353 cm-1.
1H NMR (300 MHz, CDCl3): d = 7.59 (d, J = 15.6 Hz, 1 H), 7.46 (d,
J = 8.7 Hz, 2 H), 6.90 (d, J = 9.0 Hz, 2 H), 6.26 (d, J = 15.6 Hz, 1
H), 5.52 (br s, 1 H), 3.84 (s, 3 H), 2.95 (d, J = 4.8 Hz, 3 H).
HRMS (FAB+): m/z [M + H+] calcd for C7H14NO: 128.1075; found:
128.1085.
13C NMR (125 MHz, CDCl3): d = 167.3, 160.9, 140.4, 129.5, 127.7,
118.4, 114.4, 55.5, 26.7.
Acknowledgment
This research was performed in collaboration with the Walther
Cancer Institute. We wish to acknowledge Prof. Tobias Rein for
helpful discussions and the Wolf Fellowship for financial support of
D.J.S.
HRMS (FAB+): m/z [M + H+] calcd for C11H14NO2: 192.1025;
found: 192.1011.
(E)-N-Methyl-3-(naphthalen-6-yl)acrylamide (5d)
Using the procedure described above, 5d was isolated (yield: 77%;
85 mg) as a white crystalline solid; mp 183–184 °C; Rf = 0.08 (hex-
anes–EtOAc, 7:3).
References
IR (KBr): 3269, 1655, 1618, 1560, 1384 cm-1.
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Res. Dev. 2003, 7, 362. (d) Grison, C.; Genève, S.; Halbin,
E.; Coutrot, P. Tetrahedron 2001, 57, 4903. (e) Wehlan, H.;
Dauber, M.; Fernaud, M.-T. M.; Schuppan, J.; Mahrwald,
R.; Ziemer, B.; Garcia, M.-E. J.; Koert, U. Angew. Chem.
Int. Ed. 2004, 43, 4597. (f) Sano, S.; Takemoto, Y.; Nagao,
Y. Tetrahedron Lett. 2003, 44, 8853.
1H NMR (300 MHz, CDCl3): d = 7.78 (s, 1 H), 7.73–7.63 (m, 4 H),
7.55 (dd, J = 1.5, 8.7 Hz, 1 H), 7.38 (m, 2 H), 6.84 (br s, 1 H), 6.54
(d, J = 15.9 Hz, 1 H), 2.84 (d, J = 4.2 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 166.7, 139.9, 133.7, 133.3, 132.5,
129.0, 128.4, 128.3, 127.6, 126.7, 126.5, 123.5, 121.4, 26.3.
HRMS (FAB+): m/z [M + H+] calcd for C14H14NO: 212.1075;
found: 212.1082.
(E)-3-Cyclohexyl-N-methylacrylamide (5e)
Using the procedure described above, 5e was isolated (yield: 82%;
72 mg) as a white solid; mp 82-83 °C; Rf = 0.12 (hexanes–EtOAc,
7:3).
IR (KBr): 3442, 3295, 2918, 2845, 1668, 1638, 1563, 1384 cm-1.
1H NMR (300 MHz, CDCl3): d = 6.78 (dd, J = 6.6, 15.3 Hz, 1 H),
5.70 (dd, J = 1.5, 15.3 Hz, 1 H), 5.48 (br s, 1 H), 2.88 (d, J = 4.8 Hz,
3 H), 2.10 (m, 1 H), 1.64-1.77 (m, 5 H), 1.21 (m, 5 H).
13C NMR (75 MHz, CDCl3): d = 167.3, 149.9, 121.1, 40.4, 32.2,
26.5, 26.2, 26.0.
HRMS (FAB+): m/z [M + H+] calcd for C10H18NO: 168.1388;
found: 168.1368.
(6) (a) Brandt, P.; Norrby, P.-O.; Martin, I.; Rein, T. J. Org.
Chem. 1998, 63, 1280. (b) Ando, K. J. Org. Chem. 1999, 64,
6815.
(7) Cai, M.; Huang, Y.; Zhao, H.; Song, C. J. Organomet. Chem.
2003, 682, 20.
(8) Summers, J. B.; Mazdiyasni, H.; Holms, J. H.; Ratajczyk, J.
D.; Dyer, R. D.; Carter, G. W. J. Med. Chem. 1987, 30, 574.
(9) Basavaiah, D.; Rao, A. J. Synth. Commun. 2002, 32, 195.
(10) Bellassoued, M.; Lensen, N.; Bakasse, M.; Mouelhi, S. J.
Org. Chem. 1998, 63, 8785.
(11) Brevet, J. L.; Mori, K. Synthesis 1992, 1007.
(12) El Hadrami, M.; Lavergne, J.-P.; Viallefont, P.; Itto, M. Y.
A.; Hasnaoui, A. Tetrahedron Lett. 1991, 32, 3985.
(13) Effenberger, F.; Oßwald, S. Tetrahedron: Asymmetry 2001,
12, 2581.
(E)-N-Methyloct-2-enamide (5f)
Using the procedure described above, 5f was isolated (yield: 73%;
59 mg) as a white crystalline solid; mp 40-42 °C; Rf = 0.17 (hex-
anes–EtOAc, 7:3).
IR (film): 3297, 3081, 2924, 1668, 1622, 1560 cm-1.
1H NMR (300 MHz, CDCl3): d = 6.84 (dt, J = 6.9, 15.3 Hz, 1 H),
5.75 (dt, J = 1.5, 15.3 Hz, 1 H), 5.39 (br s, 1 H), 2.88 (d, J = 5.1 Hz,
3 H), 2.17 (dq, J = 1.8, 7.5 Hz, 2 H), 1.46 (m, 2 H), 1.30 (m, 4 H),
0.89 (t, J = 7.2 Hz, 3 H).
13C NMR (125 MHz, CDCl3): d = 166.9, 144.7, 123.4, 32.0, 31.3,
28.0, 26.3, 22.5, 14.0.
HRMS (FAB+): m/z [M + H+] calcd for C9H18NO: 156.1388; found:
156.1400.
(14) Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz,
B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.
(15) Hoffman, R. V.; Madan, S. J. Org. Chem. 2003, 68, 4876.
(16) Koziara, A.; Zwierzak, A. Phosphorus, Sulfur Silicon Relat.
Elem. 1999, 149, 15.
(E)-N,4-Dimethylpent-2-enamide (5g)16
Using the procedure described above, 5g was produced in 97%
yield as measured by 1H NMR using dibenzyl ether as an internal
standard.
IR (KBr): 3276, 3085, 2959, 2851, 1673, 1628, 1560, 1356, 980
cm–1.
Synthesis 2006, No. 21, 3654–3660 © Thieme Stuttgart · New York