Search

Abstract: The reaction of formaldehyde with enantiomerically pure α-N-protected amino acid hydrazides is described. The system has been investigated in different solvents, including both aqueous formaldehyde and paraformaldehyde, with the [...]

[alpha]-Amino acids and [alpha]-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the [alpha]-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride. Key words: [alpha]-amino acid, [alpha]-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.