Ethanolamine → 2-(4-methylphenyl)oxazoline

Participants

Reaction Steps

This synthesis requires a brominated intermediate, which is prepared by a four-step process, as illustrated in FIG. 3. p-Toluic acid is first converted to N-(2-hydroxyethyl)-4-toluamide, using carbonyldiimidazole (CDI) and ethanolamine. This first intermediate is then converted to a N-[2-methanesulfonyloxy]-4-toluamide, using methanesulfonyl chloride. This second intermediate is then cyclized to form 2-(4-methylphenyl)oxazoline by processes analogous to those described in Example 7, below. This third intermediate is then brominated, using N-bromosuccinimide and benzoyl peroxide as described in Example 3, to produce 2-[(4-bromomethyl)phenyl]-oxazoline. This intermediate is then reacted with hydroxy compound [2], using a procedure similar to that described in Example 3, to give the desired compound, GERI-E6.

Provenance & Evidence