A Practical Synthesis of l-Valyl-pyrrolidine-(2R)-boronic Acid:  Efficient Recycling of the Costly Chiral Auxiliary (+)-Pinanediol

A practical synthesis of l-valyl-pyrrolidine-(2R)-boronic acid (1) is detailed. A previously disclosed synthesis of 1 (Snow, R.; Kelly, T. R.; Adams, J.; Coutts, S.; Perry, C. (Boehringer Ingelheim Pharmaceuticals, Inc.). WO 93/10127, 1993) was significantly improved by developing an efficient proce...

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Bibliographic Details
Published in:Organic process research & development 2002-11, Vol.6 (6), p.814-816
Main Authors: Gibson, Frank S, Singh, Ambarish K, Soumeillant, Maxime C, Manchand, Percy S, Humora, Michael, Kronenthal, David R
Format: Article
Language:English
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Summary:A practical synthesis of l-valyl-pyrrolidine-(2R)-boronic acid (1) is detailed. A previously disclosed synthesis of 1 (Snow, R.; Kelly, T. R.; Adams, J.; Coutts, S.; Perry, C. (Boehringer Ingelheim Pharmaceuticals, Inc.). WO 93/10127, 1993) was significantly improved by developing an efficient process for recycling the costly chiral auxiliary (+)- pinanediol.
ISSN:1083-6160
1520-586X
DOI:10.1021/op025587b