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mixture was stirred at 60 °C for 2 h. The crude residue was purified by flash chromatography
(gradient elution; hexanes-EtOAc, 9 : 1 to 3 : 1, v/v) to afford 298c (20 mg, 85%).
1 H NMR (300 MHz, CDCl3): δ 7.47-7.27 (m, 10H), 7.08 (d, J = 8.8 Hz, 2H), 6.89 (d, J = 8.8 Hz,
2H), 4.26 (d, J = 13.5 Hz, 1H), 3.92 (d, J = 7.2 Hz, 1H), 3.82 (s, 3H), 3.75 (s, 3H), 3.44 (d, J =
13.5 Hz, 1H), 3.37-3.21 (m, 2H), 2.43-2.39 (m, 1H), 2.39 (t, J = 7.5 Hz, 2H), 2.22 (quin, J = 7.5
Hz, 1H), 2.06 (d, J = 14.9 Hz, 1H), 1.48 (sex, J = 7.5 Hz, 2H), 0.87 (t, J = 7.3 Hz, 3H); 13 C NMR
(75 MHz, CDCl3): δ 172.2, 169.7, 158.5, 138.3, 138.0, 137.4, 135.2, 131.9, 131.1, 129.4, 128.3,
128.1, 127.4, 126.7, 126.3, 122.7, 114.2, 73.0, 56.7, 55.4, 52.9, 52.0, 45.2, 39.4, 29.4, 29.1, 22.5,
13.9; IR (thin film): ν 2954, 1734, 1641, 1515, 1403, 1249 cm -1 ; MS m/z (%) 548 (52), 457 (36),
425 (24), 266 (52), 105 (100); EI-HRMS calcd for C35H36N2O4 m/z [M] + 548.2675, found
548.2677.
BzN
MeO2C Bn H
5-Benzoyl-4-benzyl-1-(2-hydroxyethyl)-2-propyl-3b,4,5,6,6a,7-hexahydro-1H-1,5-
H
298d
diazacyclopenta[a]pentalene-4-carboxylic acid methyl ester (298d). Prepared by following
the general procedure R, using: 297 (20 mg, 0.043 mmol), ethanolamine (26 µL, 0.43 mmol),
AcOH (20 µL, 0.36 mmol), molecular sieves (4 Å) (50 mg). The reaction mixture was stirred at
70 °C for 1 h. The crude residue was purified by flash chromatography (gradient elution;
N
C 3H 7
hexanes-EtOAc, 3 : 1 to 2 : 1, v/v) to afford 298d (16 mg, 76%).
1 H NMR (300 MHz, CDCl3): δ 7.45-7.27 (m, 10 H), 5.65 (s, 1H), 4.20 (d, J = 13.6 Hz, 1H), 3.89
(d, J = 7.2 Hz, 1H), 3.79-3.73 (m, 4H), 3.67 (s, 3H), 3.37 (d, J = 13.5 Hz, 1H), 3.26-3.23 (m,
2H), 2.55 (dd, J = 14.4, 7.1 Hz, 1H), 2.47 (t, J = 7.8 Hz, 2H), 2.37 (quind, J = 7.2, 2.0 Hz, 1H),
2.29 (d, J = 14.3 Hz, 1H), 2.06-1.94 (bs, 1H), 1.70-1.58 (m, 2H), 1.01 (t, J = 7.4 Hz, 3H); 13 C
262
OH