Simple and rapid synthesis of N α - urethane protected β -amino alcohols and peptide alcohols employing HATU

The activation of the N"-urethane protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing 1-[bis(dimethylamino)-melhylene]-1H-1,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding β-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent IIATU for practical synthesis of β-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.