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HETEROCYCLES, Vol. 73, 2007
[5-tert-Butyloxycarbonylmethyl-1-(2’hydroxy-1’(R)’-phenylethyl)pyrrolidin-2-yl]acetic acid tert-
1
butyl ester (6d) [α]D -60° (c 2.14, CCl4). H NMR (CDCl3, 400 MHz): δ 1.21 (1H, m), 1.37 (1H, m),
1.40 (1H, m), 1. 42 (9H, s), 1.46 (9H, s), 1.71 (1H, m), 2.14 (1H, dd, J = 8.8, 15.6 Hz), 2.27 (1H, dd, J =
8.7, 15.5 Hz), 2.36 (1H, dd, J = 5.2, 10.0 Hz), 2.50 (1H, dd, J = 4.6, 11.0 Hz), 3.29 (1H, br), 3.42 (1H, dd,
J = 4.5, 8.6 Hz), 3. 44 (1H, m), 3.62 (1H, dd, J = 4.5, 11.0 Hz), 3.88 (1H, dd, J = 4.5, 11.0 Hz), 3.89 (1H,
13
dd, J = 10.0, 12.0 Hz), 7.14-7.35 (5H, m). C NMR (CDCl3, 100 MHz): δ 28.2 (CH3), 29.8 (CH2), 30.3
(CH2), 42.1 (CH2), 44.5 (CH2), 54.5 (CH), 60,4 (CH), 62.0 (CH2), 65.1 (CH), 80.5 (C), 80.7 (C), 127.9
(CHar), 128.4 (CHar), 128.8 (CHar), 136.8 (Car), 171.4 (C=O), 171.5 (C=O). IR (neat): ν (cm-1) 3438
(OH), 2976 (C-H), 1721 (C=O), 1254 (C-O), 1149 (C-C), 1080 (C-N). GC-MS (EI) m/z (%): 388 (43.6),
304 (26.7), 276 (100.0), 230 (13.9), 91 (9.1).
[5-Benzyloxycarbonylmethyl-1-(1’-(S)-phenylethyl)pyrrolidin-2-yl]acetic acid benzyl ester (6e)
[α]D +23° (c 1.00, CH2Cl2). 1H NMR (CDCl3, 300 MHz): δ 1.39 (3H, d, J = 6.8 Hz), 1.50-1.62 (2H, m),
1.69-1.87 (2H, m), 2.14 (2H, d, J = 6.8 Hz), 2.36 (1H, dd, J = 14.9, 8.7 Hz), 2.54 (1H, dd, J = 14.9, 4.7
Hz), 3.38-3.54 (2H, m), 3.96 (1H, q, J = 6.8 Hz), 5.03 (2H, s), 5.09 (2H, s), 7.17-7.37 (m, 15H); 13C NMR
(CDCl3, 75 MHz): δ 15.67 (CH3), 30.04 (CH2), 30.46 (CH2), 42.02 (CH2), 42.43 (CH2), 56.48 (CH),
58.13 (CH), 58.34 (CH), 65.70 (CH2), 65.86 (CH2), 126.72 (CHar), 127.94 (CHar), 127.95 (CHar),
127.96 (CHar), 128.01 (CHar), 128.05 (CHar), 128.34 (CHar), 128.38 (CHar), 135.88 (Car) ,136.94 (Car),
143.24 (Car), 171.86 (C=O), 171.93 (C=O). IR (neat): ν (cm-1) 2967 (C-H), 1728 (C=O), 1164 (C-C),
1082 (C-N). Anal. Calcd for C30H33NO4: C, 76.41; H, 7.05; N, 2.97. Found: C, 76.18; H, 6.37; N, 2.92.
[5-Benzyloxycarbonylmethyl-1-(2’-hydroxy-1’(R)-phenylethyl)pyrrolidin-2-yl]acetic acid benzyl
1
ester (6f) [α]D -55° (c 1.00, CH2Cl2). H NMR (CDCl3, 300 MHz): δ 1.38-1.52 (2H, m), 1.54-1.72 (2H,
m), 2.29 (1H, dd, J = 14.5, 8.5 Hz), 2.45-2.52 (2H, m), 2.67 (1H, dd, J = 14.5, 4.9 Hz), 3.18 (1H, br),
3.50-3.61 (2H, m), 3.64-3.71 (1H, m), 3.87-3.96 (2H, m), 5.11 (2H, s), 5.15 (2H, s), 7.19-7.41 (15H, m).
13C NMR (CDCl3, 300 MHz): δ 29.8 (CH2), 30.5 (CH2), 40.8 (CH2), 42.9 (CH2), 54.6 (CH), 60.4 (CH),
62.1 (CH2), 65.5 (CH), 66.3 (CH2), 66.4 (CH2), 127.9 (CHar), 128.3 (CHar), 128.3 (CHar), 128.3 (CHar),
128.5 (CHar), 128.5 (CHar), 128.6 (CHar), 128.6 (CHar), 128.7 (CHar), 135.8 (Car), 135.8 (Car), 136.7
(Car), 171.8 (C=O). IR (neat): ν (cm-1) 3448 (OH), 2955 (C-H), 1726 (C=O), 1270 (C-O), 1165 (C-C),
1080 (C-N). GC-MS (EI) m/z (%): 379 (9), 320 (36), 230 (100), 91 (62).
ACKNOWLEDGEMENTS
This work was financially supported in part by a post-doctoral grant for L. Cabral dos Santos from the