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1H), 6.52 (dd, J = 8.2, 1.8 Hz, 1H), 6.22 (s, 1H), 5.34 (d, J = 15.1 Hz, 1H), 5.11 (d, J = 15.1 Hz,
1H), 4.23 (d, J = 13.6 Hz, 1H), 3.87 (d, J = 7.3 Hz, 1H), 3.82 (s, 3H), 3.78 (s, 3H), 3.62 (s, 3H),
3.59-3.55 (m, 4H), 3.39 (d, J = 13.7 Hz, 1H), 3.36-3.30 (m, 1H), 3.18-3.12 (m, 1H), 2.42 (dd, J =
15.1, 6.9 Hz, 1H), 2.33-2.23 (m, 1H), 2.13 (d, J = 15.6 Hz, 1H), 1.82-1.92 (m, 4H); 13 C NMR
(75 MHz, CDCl3): δ 172.3, 169.9, 162.2, 149.0, 148.2, 141.0, 137.7, 137.2, 131.3, 131.1, 129.8,
129.7, 128.5, 128.3, 126.9, 126.4, 122.9, 119.3, 110.9, 110.5, 108.8, 73.1, 56.5, 56.0, 55.9, 52.2,
49.8, 48.0, 45.7, 39.4, 28.8, 25.5; IR (thin film): ν 2949, 1734, 1638, 1605, 1445, 1400 cm -1 ; MS
m/z (%) 647 (51), 556 (42), 381 (27), 151 (100), 105 (65); EI-HRMS calcd for C39H41N3O6 m/z
[M] + 647.2995; found 647.2991.
H
BzN
MeO2C Bn
H
5-Benzoyl-4-benzyl-1-(4-hydroxy-3-methoxybenzyl)-2-(pyrrolidine-1-carbonyl)-
MeO
308c
3b,4,5,6,6a,7-hexahydro-1H-1,5-diazacyclopenta[a]pentalene-4-carboxylic acid methyl ester
(308c). Prepared by following general procedure T with: 307 (35 mg, 0.068 mmol), 4-
aminomethyl-2-methoxyphenol hydrochloride (39 mg, 0.20 mmol), AcOH (80 µL). Yield 308c
(31 mg, 72%).
1 H NMR (300 MHz, CDCl3): δ 7.41-7.27 (m, 10H), 6.75 (d, J = 8.1 Hz, 1H), 6.64 (s, 1H), 6.44
(d, J = 8.1 Hz, 1H), 6.21 (s, 1H), 5.72 (bs, 1H), 5.31 (d, J = 15.0 Hz, 1H), 5.07 (d, J = 15.0 Hz,
1H), 4.22 (d, J = 13.6 Hz, 1H), 3.86 (d, J = 7.2 Hz, 1H), 3.79 (s, 3H), 3.61 (s, 3H), 3.61-3.50 (m,
4H), 3.44-3.29 (m, 2H), 3.18-3.11 (m, 1H), 2.42 (dd, J = 15.2, 7.0 Hz, 1H), 2.33-2.22 (m, 1H),
2.13 (d, J = 15.4 Hz, 1H), 1.93-1.80 (m, 4H); 13 C NMR (75 MHz, CDCl3): δ 172.2, 169.8, 162.1,
146.5, 144.8, 140.8, 137.5, 137.0, 130.9, 130.5, 129.7, 129.6, 128.4, 128.2, 126.8, 126.2, 122.7,
268
N
OH
O
N