Methanol → Methyl 2-allyloctanoate

Participants

Reaction Steps

A solution of 0.345 g (1.0 mmol) of N-methyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine in 5 ml of methanol was cooled to 0° C., 0.386 g (2.0 mmol) of NaOMe (28% solution in methanol) was added, and the mixture was stirred for 22 hours. The reaction was terminated by addition of 2 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was isolated/purified on a silica gel column to give 0.10 g (51%) of the title compound. N-(2-Allyloctanoyl)-(R)-1-phenylethylamine was formed as a byproduct in 45% yield.

Provenance & Evidence