Addition of various aryl magnesium bromides to (R) or (S)-2-(1-hydroxybutyl)phthalimide results in the formation of substituted (R) or (S)–3-hydroxy-2(1-hydroxybutyl)isoindol-1-ones which are subsequently cyclised under highly acidic conditions to give the title compounds in moderate yields.
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Single crystals of compound 10b were grown by slow evaporation of the solution in ethyl acetate / petroleum ether solvent mixture. Transparent crystal of approximate size 0.237 × 0.461 × 0.556 mm, was used for data collection on Bruker SMART APEX CCD diffractometer using Mo Kα radiation with fine focus tube with 50kV and 30mA. 2θ range = 4.04 to 57.7 °, completeness to 2θ of 57.7 ° is 90.7%. SADABS correction applied. 2 × (C18H17NO2), M = 558.65. Crystals belong to monoclinic, space group P 21, a = 8.338 (2), b = 20121 (4), c = 9.416 (2) Å, β = 109.440 (3) °, V = 1489.7(5) Å3, Z = 2, Dc = 1.245 mg m−3, μ (Mo–Kα) = 0.081 mm−1, T = 293(2) K, 8976 reflections measured, 5894 unique [I>2σ(I)], R value 0.0448, wR2 = 0.1163 (all data R = 0.0528, wR2 = 0.1208). All the data were corrected for Lorentzian, polarisation and absorption effects. SHELX-97 (ShelxTL) was used for structure solution and full matrix least squares refinement on F2.
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