1648 J. Chin. Chem. Soc., Vol. 54, No. 6, 2007
Chang et al.
(ESI, M+ + 1) calcd for C32H34NO3S 512.2259, found
512.2263; 1H NMR (500 MHz, CDCl3) d 7.69 (d, J = 8.0
Hz, 2H), 7.24 (d, J = 8.0 Hz, 2H), 7.19-7.07 (m, 10H),
6.79-6.71 (m, 4H), 4.85 (t, J = 4.5 Hz, 1H), 3.64 (s, 3H),
3.50 (t, J = 7.5 Hz, 1H), 3.03-2.98 (m, 1H), 2.89-2.83 (m,
1H), 2.56-2.49 (m, 1H), 2.47-2.41 (m, 1H), 2.43 (s, 3H),
2.32-2.26 (m, 1H), 1.78-1.68 (m, 2H); 13C NMR (125
MHz, CDCl3) d 157.35, 145.51, 143.60, 142.76, 137.54,
130.31, 129.89 (2x), 129.47 (2x), 128.39 (2x), 128.21 (2x),
128.16 (2x), 127.15 (2x), 126.89, 126.79 (2x), 126.38,
126.08, 120.13, 110.07, 64.79, 58.27, 54.96, 45.06, 34.61,
34.22, 27.50, 21.49.
36.83, 34.71, 31.80, 21.51.
2-[2-(2,6-Dimethylphenyl)ethyl]-1-methylphenylsufonyl-
3,3-diphenyl-pyrrolidine (3f)
Mp = 181-182 °C; HRMS (ESI, M+ + 1) calcd for
1
C33H36NO2S 510.2467, found 510.2465; H NMR (500
MHz, CDCl3) d 7.70 (d, J = 8.0 Hz, 2H), 7.27-7.24 (m, 4H),
7.20-7.14 (m, 3H), 7.05-6.98 (m, 5H), 6.93-6.86 (m, 3H),
4.89 (t, J = 5.0 Hz, 1H), 3.63-3.58 (m, 1H), 2.95-2.86 (m,
2H), 2.64 (dt, J = 4.5, 13.0 Hz, 1H), 2.57-2.50 (m, 1H),
2.48-2.40 (m, 1H), 2.44 (s, 3H), 1.97 (s, 6H), 1.84-1.75 (m,
1H), 1.67-1.59 (m, 1H); 13C NMR (125 MHz, CDCl3) d
145.13, 143.70, 142.97, 138.82, 136.73, 136.24 (2x), 129.51
(2x), 128.56 (2x), 128.21 (2x), 128.18 (2x), 127.83 (2x),
127.23 (2x), 126.62, 126.40 (2x), 126.02, 125.48, 65.46,
58.29, 45.05, 34.44, 33.89, 27.03, 21.48, 19.38 (2x); Anal.
Calcd for C33H35NO2S: C, 77.76; H, 6.92; N, 2.75. Found:
C, 77.96; H, 7.12; N, 3.03.
2-[2-(3-Methoxyphenyl)ethyl]-1-methylphenylsufonyl-
3,3-diphenyl-pyrrolidine (3d)
Mp = 138-140 °C; IR (CHCl3) 3446, 2916, 2846,
1600, 1491, 1337, 1155, 752, 700, 592 cm-1; HRMS (ESI,
M+ + 1) calcd for C32H34NO3S 512.2259, found 512.2262;
1H NMR (500 MHz, CDCl3) d 7.71 (d, J = 8.0 Hz, 2H),
7.28-7.02 (m, 13H), 6.65 (dd, J = 2.5, 8.0 Hz, 1H), 6.34 (d,
J = 7.5 Hz, 1H), 6.24 (s, 1H), 4.74 (t, J = 4.5 Hz, 1H), 3.72
(s, 3H), 3.55 (t, J = 8.0 Hz, 1H), 3.02-2.97 (m, 1H), 2.86
(dt, J = 8.0, 12.0 Hz, 1H), 2.45 (s, 3H), 2.43-2.37 (m, 2H),
2.18 (dt, J = 5.0, 12.0 Hz, 1H), 1.80-1.67 (m, 2H); 13C
NMR (125 MHz, CDCl3) d 159.40, 145.48, 143.51, 143.35,
143.05, 137.32, 129.61 (2x), 129.05, 128.48 (2x), 128.25
(2x), 128.21 (2x), 127.10 (2x), 126.81 (2x), 126.70, 126.16,
120.70, 113.77, 111.23, 64.26, 58.33, 55.08, 45.24, 36.50,
34.73, 32.82, 21.49; Anal. Calcd for C32H33NO3S: C,
75.11; H, 6.50; N, 2.74. Found: C, 75.32; H, 6.26; N, 2.86.
ACKNOWLEDGEMENT
The authors would like to thank the National Science
Council (NSC-95-2113-M-390-003-MY2) of the Republic
of China for financial support.
Received April 30, 2007.
REFERENCES
2-[2-(4-Methoxyphenyl)ethyl]-1-methylphenylsufonyl-
3,3-diphenyl-pyrrolidine (3e)
1. (a) Chang, M.-Y.; Pai, C.-L.; Lin, C.-Y. Tetrahedron Lett.
2006, 47, 3641. (b) Chang, M.-Y.; Pai, C.-L.; Kung, Y.-H.
Tetrahedron Lett. 2005, 46, 8463. (c) Chang, M.-Y. Lin,
C.-Y.; Hung, C.-Y. Tetrahedron 2007, 63, 3312. (d) Chang,
M.-Y.; Kung, Y.-H.; Ma, C.-C. Tetrahedron Lett. 2007, 48,
199.
Mp = 163-165 °C; IR (CHCl3) 3445, 3025, 2926,
1598, 1513, 1447, 1337, 1245, 1161, 1033, 755 cm-1; HRMS
(ESI, M+ + 1) calcd for C32H34NO3S 512.2259, found
512.2259; 1H NMR (500 MHz, CDCl3) d 7.71 (d, J = 8.5
Hz, 2H), 7.28-7.19 (m, 5H), 7.13-7.02 (m, 7H), 6.70 (d, J =
8.5 Hz, 2H), 6.65 (d, J = 8.5 Hz, 2H), 4.73 (t, J = 4.5 Hz,
1H), 3.75 (s, 3H), 3.54 (t, J = 8.0 Hz, 1H), 3.02-2.96 (m,
1H), 2.86 (dt, J = 8.0, 12.0 Hz, 1H), 2.45 (s, 3H), 2.42-2.34
(m, 2H), 2.15 (dt, J = 5.5, 13.0 Hz, 1H), 1.76-1.67 (m, 2H);
13C NMR (125 MHz, CDCl3) d 157.58, 145.49, 143.39,
143.00, 137.34, 133.98, 129.59 (2x), 129.22 (2x), 128.45,
128.45 (2x), 128.23 (2x), 128.21 (2x), 127.12 (2x), 126.81,
126.68, 126.14, 113.53 (2x), 64.30, 58.32, 55.20, 45.22,
2. (a) Chang, M. Y.; Kung, Y. H.; Chen, S. T. Tetrahedron Lett.
2006, 47, 4865. (b) Chang, M. Y.; Kung, Y. H.; Chen, S. T.
Tetrahedron 2006, 62, 10843. (c) Chang, M. Y.; Kung, Y. H.;
Ma, C. C.; Chen, S. T. Tetrahedron 2007, 63, 1339. (d)
Chang, M. Y.; Lin, C. Y.; Wu, T. C. Tetrahedron 2006, 62,
12334.
3. (a) Lyle, R. E.; Lyle, G. G. J. Am. Chem. Soc. 1954, 76, 3536.
(b) Nagai, Y.; Uno, H. Chem. Pharm. Bull. 1979, 27, 2056.
(c) Finney, Z. G.; Riley, T. N. J. Med. Chem. 1980, 23, 895.