Diisopropylamine → HCID 23033740, compound

Temperature

0 °C

A solution of n-butyllithium in hexane (1.6 M) (13.75 ml, 22 mmol) was added dropwise into a solution of diisopropylamine (3.08 ml, 22 mmol) in tetrahydrofuran (50 ml) with ice-cooling. After stirring at 0° C. for 30 minutes, it was cooled to −78° C., and then a solution of 1-methylpyrrolidin-2-one (1.98 g, 20 mmol) in THF (20 ml) was added dropwise. After stirring at −78° C. for 30 minutes, a solution of benzyl chloromethyl ether (3.76 g, 24 mmol) in THF (30 ml) was added dropwise. After stirring at −78° C., water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane; 4/1) to give the title compound (4.14 g, 94%) as a colorless oily matter.

1. temperaturecooling
2. temperatureit was cooled to −78° C.
3. stirringAfter stirring at −78° C. for 30 minutes
4. stirringAfter stirring at −78° C.
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with aqueous sodium bicarbonate and brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane; 4/1)

ORD record

ord-c100ef6749af4f9fb73be68b1cc8e978

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569570B2