Optical Resolution, Stereoselective Synthesis, and Crystal Structure of 9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate

Abstract

9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N‐p‐toluenesulfonylglutamic acid. Optical pure 1 was also effective diastereoselective synthesized using benzaldehye as steric hindrance agent from the chiral starting material, (S) or (R)‐mandelic acid. The structure of the title compound was first elucidated by X‐ray analysis.

Keywords:

• Crystal structure
• optical resolution
• stereoselective synthesis

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 30271492).