187934-90-3

Upstream product

• 200629-39-6 (4R,5S)-4-(4-methoxyphenyl)-5-(2-pyridyl)-2-pyrrolidinone 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 80500-11-4 N-(diphenylmethylene)-1-(pyridin-2-yl)methanamine 
• 200629-37-4 (4R,5S)-1-acetoxymethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-2-pyrrolidinone 
• 637-69-4 4-Methoxystyrene 

Downstream Products

• 1098300-19-6 (2S,3R)-N₁-(5-chloro-1,3-benzoxazol-2-yl)-3-(4-methoxyphenyl)-2-(pyridin-2-yl)-1-pyrrolidinecarbothioamide 

Relevant academic research and scientific papers

Practical synthesis of an enantiomerically pure trans-4,5-disubstituted 2-pyrrolidinone via enzymatic resolution. Preparation of the LTB4 inhibitor BIRZ-227

A practical synthesis of the enantiomerically pure BIRZ-227 (1), a LTB4 inhibitor, has been developed. The key steps include the effective synthesis of the trans-diarylpyrrolidinone (±)-8 and the enzymatic resolution of N- acetoxymethyl pyrrolidinone (±)-10 by immobilized Lipase Novozym 435. Reduction of pyrrolidinone (+)-8 with borane and subsequent coupling with chlorobenzoxazole 2 furnished BIRZ-227 in high enantiomeric purity (99% ee). The overall process described herein required no chromatographic separation and is amenable to the preparation of multikilogram quantities of the desired drug candidate in a cost-effective manner.

Resolution and assignment of the absolute stereochemistry of a trans-2,3-diarylpyrrolidine LTB4 inhibitor intermediate

1,3-Cycloaddition of an azaallyl anion with 4-methoxystyrene furnishes the corresponding racemic trans-pyrrolidine. Resolution of both enantiomers was accomplished by fractional crystallization with the inexpensive diacetone-2-keto-L-gulonic acid. The abs