Tetrahydrofuran → Methyl 2-allyloctanoate

Participants

Reaction Steps

A solution of 0.374 g (1.0 mmol) of N-isopropyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine ((1R,2S):(1R,2R)=77.6:22.4) in 5 ml of THF 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 1 hour. The reaction was terminated by addition of 2 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate (30 ml×2). The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was quantitated by GC. Thus was obtained 0.165 g (83%, 55.3% ee) of the title compound.

Provenance & Evidence