Preparation of Some Derivatives of N‐tert‐Butyldecahydro‐3‐isoquinoline Carboxamide

Abstract

N‐tert‐Butyldecahydro‐3‐isoquinoline carboxamide (1) is a key structural fragment present in a variety of medicinally important HIV protease inhibitors. Derivatives of this carboxamide were prepared by alkylation with either 2‐iodoethanol, allyl bromide, or bromoacetaldehyde dimethylacetal. The corresponding aldehyde of the dimethylacetal derivative was prepared by reaction with BBr₃ in CH₂Cl₂.

Keywords:

• Acetal cleavage
• aldehyde
• HIV protease inhibitors
• N‐tert‐butyldecahydro‐3‐isoquinoline carboxamide

Acknowledgments

We thank Pfizer Global Research and Development (La Jolla, CA) for the generous gift of N‐tert‐butyldecahydro‐3‐isoquinoline‐carboxamide. The authors thank the donors of the American Chemical Society Petroleum Research Fund for support of this research.