Abstract A highly efficient one-pot procedure was developed for the synthesis of 3- trimethylsilylpropynamides by acylation of amines with trimethylsilylpropynoyl chloride generated in situ. Selective N-acylation and N, O-bis-acylation of ß-amino alcohols with formation of, respectively, N-(hydroxyalkyl) propynamides and 2-methyl-2-[3-(trimethylsilyl) propynoylamino] propyl 3-(trimethylsilyl) propynoate were accomplished with high yields.