Ethyl Acetate → HCID 10923105, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of potassium tert-butoxide (3.42 g, 30 mol) in THF which was warmed at 60° C. was added a solution of methyl N-[(allyloxy)carbonyl]-N-(4-ethoxy-4-oxobutyl)-L-alaninate(4.60 g, 15 mmol) in THF (30 ml) and after stirring for 1 minute, the reaction solution was poured into an aqueous sodium dihydrogenphosphate solution (1M, 50 ml). The solution was adjusted to pH 2–3 and thereto was added ethyl acetate. After separating the mixture with a separating funnel, the aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography to give 1-allyl 4-ethyl (2S)-2-methyl-3-oxo-1,4-piperidinedicarboxylate (2.03 g) and 1-allyl 4-methyl (2S)-2-methyl-3-oxo-1,4-piperidinedicarboxylate (1.20 g).

Provenance & Evidence