AI Article Synopsis
- A new method for producing (S)-(+)-3-aminomethyl-5-methylhexanoic acid, also known as Pregabalin, is presented.
- The process involves a crucial step where a specific acid salt undergoes asymmetric hydrogenation using a rhodium catalyst, resulting in a high enantiomeric excess for the desired compound.
- A follow-up hydrogenation of the product's nitrile using a nickel catalyst yields Pregabalin with excellent yield and purity.
Article Abstract
A concise enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid (1, Pregabalin) has been developed. The key step is the asymmetric hydrogenation of a 3-cyano-5-methylhex-3-enoic acid salt 2 with a rhodium Me-DuPHOS catalyst, providing the desired (S)-3-cyano-5-methylhexanoate 3 in very high ee. Subsequent hydrogenation of the nitrile 3 with a heterogeneous nickel catalyst provides Pregabalin 1 in excellent overall yield and purity.
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| http://dx.doi.org/10.1021/jo034397b | DOI Listing |
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