Chlorotrimethylsilane → ethyl N-trimethylsilylpiperidin-4-ylcarboxylate

Participants

Reaction Steps

Under a nitrogen atmosphere a stirred solution of 50.0 grams (0.313 mole) of ethyl piperidin-4-ylcarboxylate in 300 mL of diethyl ether was cooled to 0° C. and 33.8 grams (0.338 mole) of triethylamine was added in one portion. To this was added dropwise during a 30 minute period a solution of 34.6 grams (0.338 mole) of trimethylsilyl chloride in 100 mL of diethyl ether. Upon completion of the addition the reaction mixture was stirred for five hours, then it was filtered to remove triethylamine hydrochloride. The filtrate was concentrated under reduced pressure to a residue. The residue was then dissolved in 200 mL of hexane in which it was allowed to stand for about two hours under a nitrogen atmosphere. The solution was filtered and concentrated under reduced pressure, yielding 66.9 grams of ethyl N-trimethylsilylpiperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence