Stereoselective Synthesis of the Optical Isomers of a New Muscarinic Receptor Antagonist, HL-031120

We present here a practical stereoselective synthetic method to produce enantiopure isomers of a new muscarinic receptor antagonist, HL-031120 (3-quinuclidinyl-2′-cyclopentyl-2′-hydroxy-2′-phenylacetate, I). Four optical isomers were effectively by stereoselective synthesized using pivaldehyde as st...

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Bibliographic Details
Published in:Synthetic communications 2006-07, Vol.36 (13), p.1815-1822
Main Authors: Liu, Yu-Min, Liu, He, Zhong, Bo-Hua, Liu, Ke-Liang
Format: Article
Language:English
Subjects:
Muscarinic receptor antagonist
stereoselective synthesis
tertiary α-hydroxy acid
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Summary:We present here a practical stereoselective synthetic method to produce enantiopure isomers of a new muscarinic receptor antagonist, HL-031120 (3-quinuclidinyl-2′-cyclopentyl-2′-hydroxy-2′-phenylacetate, I). Four optical isomers were effectively by stereoselective synthesized using pivaldehyde as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The isomers were obtained with 70-76% yields in 98-99% e.e.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910600602453