Practical asymmetric synthesis of a potent Cathepsin K inhibitor. Efficient palladium removal following Suzuki coupling

…, P O'Shea, P Prasit, J Robichaud, R Tillyer…

Index: Chen, Cheng-yi; Dagneau, Philippe; Grabowski, Edward J.J.; Oballa, Renata; O'Shea, Paul; Prasit, Peppi; Robichaud, Joel; Tillyer, Rich; Wang, Xin Journal of Organic Chemistry, 2003 , vol. 68, # 7 p. 2633 - 2638

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Citation Number: 61

Abstract

A large-scale, chromatography-free synthesis of a potent and selective Cathepsin K inhibitor 1 is reported. The key asymmetric center was installed by addition of (R)-pantolactone to the in situ-generated ketene 4a. The final step of the convergent synthesis of 1 was completed via Suzuki coupling of aryl bromide 7a with unprotected aryl piperazine boronic acid 13. Residual palladium and iron generated in the Suzuki coupling were efficiently removed ...