ChemInform Abstract: Practical Synthesis of an Enantiomerically Pure trans-4,5-Disubstituted 2-Pyrrolidinone via Enzymatic Resolution. Preparation of the LTB4 Inhibitor BIRZ-227.

✍ Scribed by N. K. YEE; L. J. NUMMY; D. P. BYRNE; L. L. SMITH; G. P. ROTH

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199824106

✦ Synopsis

Practical Synthesis of an Enantiomerically Pure trans-4,5-Disubstituted 2-Pyrrolidinone via Enzymatic Resolution. Preparation of the LTB 4 Inhibitor BIRZ-227. -The efficient synthesis of rac. (II) in a simple one-pot procedure was already described. A novel enzymatic resolution of its rac derivative (V) by immobilized Lipase Novozym 435 is followed by a nonchromatographic separation of the resolved mixture. The following processes lead to the title compound (VI) in high enantiomeric purity. Such compounds can be useful for the treatment of various inflammatory disorders. The overall synthesis for (VI) described, is amenable to the preparation of multikilogram quantities in a cost-effective manner.

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