Tetrahydrofuran → Methyl 2-allyloctanoate

Participants

Reaction Steps

A solution of 25.12 g (67.5 mmol) of N-isopropyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine ((1R,2S):(1R,2R)=77:23) in 338 ml of THF was cooled to −10° C., 26.1 g (135 mmol) of NaOMe (28% solution in methanol) was added dropwise and, after completion of the addition, the mixture was further stirred for 45 minutes. The reaction was terminated by addition of 120 ml of 1 N hydrochloric acid, and the product was extracted with hexane (100 ml×2). The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off to give 25.90 g of a crude product. This was purified on a silica gel column to give 12.32 g (92%, 54% ee) of the title compound.

Provenance & Evidence