Methyl iodide → HCID 13022015, compound

Temperature

-78 °C

Diisopropyl amine (0.12 moles) was added to a flask and diluted with 40 mL of toluene. The resultant was cooled to −78° C. under nitrogen, and then a hexane solution of n-butyl lithium (0.11 moles) was added thereto, followed by stirring at −78° C. for 1 hour. To this, 2-morpholinopropionic acid ethyl ester (0.105 moles) was added and the resultant was further stirred for 1 hour, and iodomethane (0.21 moles) was added thereto and after the temperature was restored to room temperature, 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 evaporated, and the residue was purified by column chromatography (hexane/ethyl acetate=4/1) to obtain α-morpholino isobutyric acid ethyl ester (0.55 moles).

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

ORD record

ord-d68203b9357b4bdc8130cf4328b23ee3

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691352B2