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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 9
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Original Articles

Regio and Stereospecific Synthesis of Bicyclic Pyrrolidines

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Pages 1321-1328 | Received 06 Nov 1992, Published online: 24 Sep 2006

References

  • Grigg , R. , Nimal Gunaratne , H. Q. and Sridharan , V. 1987 . Tetrahedron , 43 : 5887
  • Barr , D. A. , Grigg , R. , Nimal Gunaratne , N. Q. , Kemp , J. , Mc Meekin and Sridharan , V. 1988 . Tetrahedron , 44 : 557
  • Kanemasa , Sh. , Yoshiota , M. and Tsuge , O. 1989 . Bull. Chem. Soc. Jpn. , 62 : 869
  • Tsuge , O. , Kanemasa , Sh. and Yoshiota , M. 1988 . J. Org. Chem. , 53 : 1384
  • Amornraksa , K. , Barr , D. , Donegan , J. , Grigg , R. , Ratanankul , P. and Sridharan , V. 1989 . Tetrahedron , 45 : 4649
  • Barr , D. A. , Grigg , R. and Sridharan , V. 1989 . Tetrahedron Letters , 30 : 4727
  • Grigg , R. and Kemp , J. 1980 . Tetrahedron Letters , 41 : 2461
  • Tsuge , O. , Ueno , K. , Kanemasa , Sh. and Yorozu , K. 1986 . Bull. Chem. Soc. Jpn. , 59 : 1809
  • Grigg , R. , Kemp , J. , Sheldrik , G. and Trotter , J. 1978 . J. Chem. Soc. Chem. Comm. , : 109
  • 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)
  • Amornraksa , K. , Grigg , R. , Nimal Gunaratne , H. Q. , Kemp , J. and Sridharan , V. 1987 . J. Chem. Soc. Perkin Trans. , 1 : 2285
  • Márquez , A. , Rodríguez , H. , Morales , E. , Quintanar , C. and Chuaqui , C. A. 1991 . Bol. Soc. Chil. Quim. , 36 : 43
  • 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
  • 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).
  • 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
  • Grigg , R. 1987 . Chem. Soc. Rev. , 16 : 89

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