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Synthesis 1988; 1988(1): 40-44
DOI: 10.1055/s-1988-27459
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Asymmetric Synthesis of 2-Substituted (4S)-4-Aminopyrrolidines. SN2 Displacement at the 4-Position of the Pyrrolidine Moiety

Terry Rosen* , Stephen W. Fesik, Daniel T. W. Chu, André G. Pernet
  • *Anti-infective Research Division, Abbott Laboratories, Abbott Park, IL 60064, USA
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Publication Date:
12 September 2002 (online)

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The trans-disubstituted-N-benzyl pyrrolidine 10 is prepared in enantiomerically homogeneous form from cis-4-hydroxy-D-proline (4) in an efficient sequence. The key step involves an SN2 displacement of the methanesulfonate of alcohol 5 with azide ion and occurs without participation of the basic ring nitrogen. The stereochemical outcome, which is contrary to that reported for the related systems 15 and 16, suggests that a mechanism involving the proposed intermediate 19a is improbable. The cis-derivative 14 is prepared by an identical sequence of reactions beginning with trans-4-hydroxy-L-proline. Compound 10 is the precursor to the potent DNA gyrase inhibitor 1 and several related analogs.

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