Methyl iodide → Ethyl 4-methyl-3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A milky solution of 7.75 g (69.02 mmol) of potassium tert-butylate in 125 ml of THF was cooled (0° C.) and treated portion wise with 10.44 g (34.00 mmol) of ethyl-N-benzyl-3-oxo-4-piperidin-carboxylate hydrochloride so the temperature did not rise over 5° C. After 1 h at RT, the reaction was cooled (0° C.) and ad treated slowly with 5.07 ml (35.70 mmol) of iodomethane in 4 ml of THF. After 4.5 h at RT, the reaction was cooled (0° C.) and neutralized with 40 ml of aqueous saturated NH4Cl solution. The aqueous phase was extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaCl, dried over Na2SO4 and evaporated to give 4.97 g (53%) of the titled compound as orange oil. MS: 276.1 (MH+).

Provenance & Evidence