174
A. Demeter et al. / Journal of Molecular Structure 471 (1998) 161±174
3.2.6. (1 0S,3S,6R)-2-(1 0-carboxy-3 0-phenylpropyl)-3-
methyl-hexahydro-pyrrolo[1,2a]pyrazine-1,4-dione
(3a) and (1 0R,3S,6R)-2-(1 0-carboyx-3 0-
phenylpropyl)-3-methyl-hexahydro-
pyrrolo[1,2a]pyrazine-1,4-dione (3 0a)
Â
of us (AD) is indebted to Dr. Cs. Szantay, Jr. for his
Â
continued supervision and help on the NMR structural
investigations as well as his invaluable comments and
criticism during preparation of the manuscript.
2a ! 3a,3 0a Yield (79%), m.p. 157±1638C, [a]D25 1
67,88 (c l, methanol), the ratio 3a/3 0a was about 15/1
based on NMR. MS m/z (rel. int %): 330(3) M1.,
226(78), 208(45), 167(20), 153(19), 126(24),
117(27), 97(32), 91(100), 70(77); IR (cm21): 1722,
1673, 1635, 1464, 1189, 735, 702. 2 0a ! 3a,3 0a
Yield (40%), the ratio 3a/3 0a was about 3/7 based
on NMR. MS m/z (rel. int %): 330(8) M1., 226(45),
208(35), 167(18), 117(34), 91(100), 70(64); IR
(cm21): 2980, 1736, 1670, 1453, 1189, 753, 701.
Crystal data of 3a: C18H22N2O4, tetragonal, P41212,
References
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Ê
Ê
Ê 3
a 9.265(1) A, c 39.089(4) A, V 3355.4(6) A ,
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Z 8, Dx 1.308 Mg m23, m 0.762 mm-1, CAD4
Ê
diffractometer, (Cu Ka radiation, l 1.5418 A) at
293(2) K. Re®nement on F2, R1 0.0539 and wR2
0.1334 for all 2067 data.
3.2.7. (1 0S,3S,6R)-3-(4-amino-butyl)-2-(1 0-carboxy-
3 0-phenylpropyl)-hexahydro-pyrrolo[1,2a]pyrazine-
1,4-dione (3b)0 and (1 0R,3S,6R)-3-(4-amino-butyl)-2-
(1 0-carboxy-3 -phenylpropyl)-hexahydro-
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pyrrolo[1,2a]pyrazine-1,4-dione (3 0b)
2b ! 3b,3 0b Yield (97%), m.p. 120±1458C,
[a]D25 1 49.08 (c l, methanol), the ratio 3b/3 0b was
about 9/1 based on NMR. MS m/z (rel. int %): 388(3)
M1., 283(23), 224(47), 208(36), 179(30), 117(47),
91(100), 70(95); IR (cm21): 2953, 1662, 1454, 1383,
1201, 752, 701.
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Acknowledgements
The authors wish to thank Dr. B. HegeduÈs for the IR
spectra, J. Brlik for the MS measurements and
 Â
L. Parkanyi for the X-ray crystallographic data. One