Chemoenzymatic preparation of non-racemic N-Boc-piperidine-3,5-dicarboxylic acid 3-methyl esters and their 5-hydroxymethyl derivatives

✍ Scribed by Hans Iding; Beat Wirz; Rosa-Marı́a Rodrı́guez Sarmiento

• Book ID: 104359834
• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 196 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00283-0

✦ Synopsis

For the synthesis of (R,R)-and (S,S)-N-Boc-5-hydroxymethyl-piperidine-3-carboxylic acid methyl ester as important basic units for potential inhibitors of aspartyl proteases, the respective non-racemic 3,5-dicarboxylic acid monomethyl esters were prepared as key intermediates from a cis,trans-mixture of the respective diester by several consecutive enzymatic reactions using Lipase AY, Chirazyme L-3, Hydrolase ESP-ESL-1064 and pig liver esterase.