The first stage of this study required scalable enzymatic methods for site-specific C-H hydroxylation of inexpensive 2-and 3-carboxylated piperidines 11 and 10. We have previously reported the gram scale syntheses of 14 and 17. However, a scalable and inexpensive synthesis of other building blocks with alternative hydroxylation patterns was still needed. trans-4-Proline hydroxylase (trans-P4H), a 2-ketoglutarate (a-KG) dependent dioxygenase with C4 hydroxylation