Abstract
A short synthesis of N-protected 1,2,5,6-tetrahydro-3-pyridinylalanine derivatives (8–10) was accomplished using a simple procedure of quaternization of (3-pyridyl)alanine 6 with benzyl bromide followed by reduction with NaBH4. Amino acid 10 was then converted to thrombin inhibitor UK-239,326 (2), which required the sequential functionalization of four amines to give four different functional groups (viz., sulfonamide, carboxamide, guanidine, and methylamine).
ACKNOWLEDGMENT
We thank our colleagues for their expert and enthusiastic technical assistance: Yvonne Ailwood, Leena Patel, and Anthony Pomeroy. We also thank members of the Physical Sciences Group for spectroscopic and analytical services.