Methyl iodide → alpha-Diethylamino isobutyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Diisopropyl amine (0.15 moles) was added to a flask and diluted with 50 mL of toluene. The resultant was cooled to −78° C. under nitrogen, and then a hexane solution of n-butyl lithium (0.13 moles) was added thereto, followed by stirring at −78° C. for 1 hour. Further, the mixture was heated to 0° C. and stirred for 1 hour. To this, 2-diethylaminopropionic acid ethyl ester (0.11 moles) was added and the resultant was further stirred for 1 hour, and iodomethane (0.23 moles) was added thereto, and then the temperature was restored to room temperature and the mixture was stirred for 1 hour. The reaction mixture was quenched with ice water, extracted with ethyl acetate and washed with a saturated sodium chloride aqueous solution, and then the organic layer was dried over magnesium sulphate. The solvent was distilled away, and then the residue was purified by column chromatography (hexane/ethyl acetate=4/1) to obtain α-diethylamino isobutyric acid ethyl ester (0.50 moles).

Provenance & Evidence