Regio and Stereospecific Synthesis of Bicyclic Pyrrolidines

References

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• 3b: Recrystallized from benzene/petroleum ether (60–80). Rf = 0.78 in ethyl acetate : di-n-butyl ether (37.5 : 62.5, v/v). 1H-NMR (acet-d6) ppm: 8.33 (d, Jd = 10 Hz, 2H); 8.13–7.37 (m, 7H); 4.62 (s, 1H); 3.78 (s, 3H); 3.05 (s, 1H); 1.33 (s, 3H). IR (KBr) cm−1: 3390 (NH); 1866–1766 (C═O anhydride); 1739 (C═O ester); 1391 (Me); 1527 and 1353 (NO2)
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• Amornraksa , K. , Grigg , R. , Nimal Gunaratne , H. Q. , Kemp , J. and Sridharan , V. 1987 . J. Chem. Soc. Perkin Trans. , 1 : 2285
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• A crystal of dimension 0.15 × 0.15 × 0.20 mm recrystallized from benzene was used for X-ray diffraction studies. Crystal data: C21H18N2O7, FW = 410.39, monoclinic, P21/c, a = 10.293(2), b = 10.078(2), c = 18.424(5) Å, ß = 96.86(2)°, V = 1897.6(1.1) Å3, z = 4, dcak = 1.436 g cm−3, F(000) = 856, λ = 0.71073 Å, μ = 1.023 cm−1. Intensity measurements with 2 θ ≤ 48°, using variable speed ω −2θ scans at room temperature with grafite monochromated Mo Kα radiation on an Enraf-Nonius CAD 4 diffractometer. The intensities of 6340 reflections were measured, whilst three standard reflections measured every 2 hours showed no decay. After corrections for Lorentz and polarization effects, averaging of equivalent reflections gave 3176 independent reflections of which 1511 with 1.5 δ (1) were considered observed. The structure was solved using the direct methods (MULTAN 11/82) as incorporated in the Enraf-Nonius SDP programs on a MICROWAX II computer. The positional and anisotropic thermal parameters of non-hydrogen atoms were refined by full matrix least-square which minimized the function w (|F0|-|Fc|). The H atom bonded to the Pyrrolidine N atom was located in the difference Fourier and the other H atoms were added at calculated positions and were given isotropic thermal parameters equivalent to 1.3 × Biso, equiv of the atom to which they were attached. Refinement with 271 parameters converged at R = 0.042, Rw = 0.050 with goodness of fit = 1.148
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• 6b: MP = 150–151°C. Analysis for C, H and N in good agreement with the calculated values. Ir (KBr) cm−1: 3390 (NH); 1730 (broad); 1520 and 1353 (NO2); 1389 (Me). 1H-RMN (CDCl3) ppm: 8.20 (d, 2H); 7.95–7.68 (m, 2H); 7.63–7.15 (m, 5H); 4.10 (s, 2H); 3.78 (s, 3H); 3.75 (s, 3H); 3.42 (s, 3H); 3.37 (s, 1H); 1.28 (s, 3H).
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• 3′b: Rf = 0.070 in ethyl acetate : di-n-butylether (37.5 : 62.5, v/v). IR (KBr) cm−1: 3367, 1824, 1745, 1613, 1527 and 1351
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