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Stereoselective lithiation and carboxylation of Boc-protected bicyclopyrrolidine: Synthesis of a key building block for HCV protease inhibitor telaprevir

Organic Process Research and Development, ISSN: 1520-586X, Vol: 18, Issue: 10, Page: 1234-1244
2014
  • 24
    Citations
  • 0
    Usage
  • 31
    Captures
  • 1
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    24
    • Citation Indexes
      24
  • Captures
    31
  • Mentions
    1
    • News Mentions
      1
      • News
        1

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Article Description

A stereoselective process for the manufacture of bicyclopyrrolidine 7 to 2 has been developed. The process utilizes a stereoselective lithiation/carboxylation sequence. The achiral diamine ligand DPBP induces excellent diastereocontrol, and resolution with (S)-THNA provides the corresponding salt of 8 in high er and dr. Subsequent processing of 8 gives 2 as the oxalate salt in an overall yield of 27% from 7 (based on total molar charge of 7). Compound 2 was obtained with high chemical and chiral purities. The process was successfully demonstrated on >100 kg scale.

Bibliographic Details

Gerald J. Tanoury; Minzhang Chen; Yong Dong; Raymond Forslund; Valdas Jurkauskas; Andrew D. Jones; Daniel Belmont

American Chemical Society (ACS)

Chemistry

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