Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine

Monomethylamine and N-benzyl-N-methylamine were used as nucleophiles in the amination of the bromoethylester of cyclopentano-phosphatidic acid. The former reagent led to extensive aminolysis and the quantitative formation of N-methylpalmitamide, rather than the desired cyclopentano-phosphatidyl-N-methylethanolamine. However, the method of Shapiro and Rabinsohn (1964. Biochemistry. 3:603-605), in which N-benzyl-N-methylamine was used as a nucleophile, was adapted for a successful synthesis.