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Prepared by following general procedure T with: 307 (30 mg, 0.058 mmol), C-
cyclopropylmethylamine (15 µL, 0.17 mmol), AcOH (70 µL). Yield 308k (22 mg, 69%).
1 H NMR (300 MHz, CDCl3): δ 7.45-7.27 (m, 10H), 6.20 (s, 1H), 4.24 (d, J = 13.6 Hz, 1H), 4.06
(dd, J = 14.1, 7.0 Hz, 1H), 3.89 (d, J = 7.4 Hz, 1H), 3.81 (dd, J = 14.1, 6.8 Hz, 1H), 3.70-3.60
(m, 4H), 3.63 (s, 3H), 3.41 (d, J = 13.7 Hz, 1H), 3.34 (dd, J = 10.1, 8.3 Hz, 1H), 3.23-3.17 (m,
1H), 2.58 (dd, J = 14.9, 6.8 Hz, 1H), 2.37-2.27 (m, 1H), 2.25 (d, J = 14.6 Hz, 1H), 2.00-1.88 (m,
4H), 1.16-1.02 (m, 1H), 0.49-0.38 (m, 2H), 0.23-0.18 (m, 2H); 13 C NMR (75 MHz, CDCl3): δ
172.3, 169.7, 162.3, 140.3, 137.6, 137.1, 131.0, 129.6, 129.4, 128.4, 128.2, 126.8, 126.3, 122.3,
108.5, 73.0, 56.3, 52.1, 51.0, 45.5, 39.3, 29.0, 12.6, 3.8, 3.5; IR (thin film): ν 2948, 1734, 1638,
1609, 1445, 1400 cm -1 ; MS m/z (%) 551 (36), 460 (37), 389 (19), 105 (100); EI-HRMS calcd for
C34H37N3O4 m/z [M] + 551.2784; found 551.2768.
H
BzN
MeO2C Bn
H
N
CO 2Me
5-Benzoyl-4-benzyl-1-methoxycarbonylmethyl-2-(pyrrolidine-1-carbonyl)-3b,4,5,6,6a,7-
308l
hexahydro-1H-1,5-diazacyclopenta[a]pentalene-4-carboxylic acid methyl ester (308l).
Prepared by following general procedure T with: 307 (24 mg, 0.047 mmol), glycine methyl ester
hydrochloride (18 mg, 0.14 mmol), AcOH (70 µL) and Et3N (19 µL, 0.14 mmol). Yield 308l (21
mg, 79%). Note: Et3N was added to help dissolve the insoluble hydrochloride salt of the primary
amine.
1 H NMR (300 MHz, CDCl3): δ 7.45-7.27 (m, 10H), 6.32 (m, 1H), 4.98 (d, J = 17.3 Hz, 1H), 4.67
(d, J = 17.3 Hz, 1H), 4.23 (d, J = 13.6 Hz, 1H), 3.92 (d, J = 7.4 Hz, 1H), 3.72 (s, 3H), 3.65 (s,
3H), 3.71-3.58 (m, 4H), 3.40 (d, J = 13.5 Hz, 1H), 3.38-3.32 (m, 1H), 3.24-3.18 (m, 1H), 2.52
(dd, J = 15.1, 7.1 Hz, 1H), 2.39-2.29 (m, 1H), 2.18 (d, J = 15.5 Hz, 1H), 2.03-1.86 (m, 4H); 13 C
274
O
N