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H
BzN
MeO2C Bn
H
308e
5-Benzoyl-4-benzyl-1-[2-(4-hydroxyphenyl)ethyl]-2-(pyrrolidine-1-carbonyl)-3b,4,5,6,6a,7-
hexahydro-1H-1,5-diaza-cyclopenta[a]pentalene-4-carboxylic acid methyl ester (308e).
Prepared by following general procedure T with: 307 (29 mg, 0.056 mmol), 4-(2-aminoethyl)-
phenol (23 µL, 0.17 mmol), AcOH (70 µL). Yield 308e (22 mg, 63%).
1 H NMR (300 MHz, CDCl3): δ 7.44-7.41 (m, 5H), 7.34-7.27 (m, 5H), 6.75 (d, J = 8.3 Hz, 1H),
6.62 (d, J = 8.3 Hz, 1H), 6.19 (s, 1H), 4.35-4.15 (m 2H), 4.22 (d, J = 13.6 Hz, 1H), 3.82 (d, J =
7.2 Hz, 1H), 3.66 (s, 3H), 3.63-3.53 (m, 4H), 3.39 (d, J = 13.6 Hz, 1H), 3.28 (dd, J = 10.2, 8.2
Hz, 1H), 3.03-2.97 (m, 1H), 2.89-2.76 (m, 2H), 2.29-2.16 (m, 2H), 1.98-1.86 (m, 4H), 1.82 (d, J
= 14.5 Hz, 1H); 13 C NMR (75 MHz, CDCl3): δ 172.2, 169.8, 162.0, 154.8, 141.1, 137.6, 137.0,
130.9, 130.1, 130.0, 129.7, 128.8, 128.5, 128.2, 126.8, 126.3, 122.1, 115.2, 109.1, 73.1, 56.3,
52.1, 48.7, 45.2, 39.3, 37.1, 28.2, 25.4; IR (thin film): ν 3237, 2950, 1733, 1601, 1447 cm -1 ; MS
m/z (%) 617 (18), 526 (22), 351 (11), 335 (9), 105 (100); EI-HRMS calcd for C38H39N3O5 m/z
[M] + 617.2890; found 617.2875.
H
BzN
MeO2C Bn
H
308f
5-Benzoyl-4-benzyl-1-(3-morpholin-4-ylpropyl)-2-(pyrrolidine-1-carbonyl)-3b,4,5,6,6a,7-
hexahydro-1H-1,5-diaza-cyclopenta[a]pentalene-4-carboxylic acid methyl ester (308f).
Prepared by following general procedure T with: 307 (34 mg, 0.066 mmol), 3-Morpholin-4-yl
propylamine (29 µL, 0.20 mmol), AcOH (80 µL). Yield 308f (16 mg, 39%).
1 H NMR (300 MHz, CDCl3): δ 7.45-7.28 (m, 10H), 6.21 (s, 1H), 4.23 (d, J = 13.7 Hz, 1H), 4.18-
N
N
270
O
O
N
N
N
OH
O