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
- 24Citations
- 31Captures
- 1Mentions
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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.
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