Methyl iodide → alpha-Diethylamino isobutyric acid ethyl ester

Temperature

-78 °C

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).

1. temperatureFurther, the mixture was heated to 0° C.
2. stirringstirred for 1 hour
3. stirringthe resultant was further stirred for 1 hour
4. customwas restored to room temperature
5. stirringthe mixture was stirred for 1 hour
6. customThe reaction mixture was quenched with ice water
7. extractionextracted with ethyl acetate
8. washwashed with a saturated sodium chloride aqueous solution
9. dry with materialthe organic layer was dried over magnesium sulphate
10. distillationThe solvent was distilled away
11. customthe residue was purified by column chromatography (hexane/ethyl acetate=4/1)

ORD record

ord-20235ea8a37441d89f1d69ca57f39630

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691352B2