Diisopropylamine → HCID 21100538、化合物

温度

0 °C

A solution (400 mL) of diisopropylamine (26.9 g) in tetrahydrofuran was cooled to −5° C. and 1.57 M n-butyllithium hexane solution (154 ml) was added dropwise to the solution. After stirring at 0° C. for 30 min, the mixture was cooled to −78° C. and a solution (50 mL) of N,N-diethyl-2,3-dimethylbenzamide (45.1 g) in tetrahydrofuran was added dropwise. After stirring at −78° C. for 1 hr, a solution (50 mL) of 1-benzyl-3-cyanopyrrolidine (37.18 g) in tetrahydrofuran was added dropwise. After completion of the dropwise addition, the reaction mixture was heated to room temperature and the mixture was stirred overnight at room temperature. The mixture was further stirred under reflux for 1 hr and the reaction mixture was concentrated to about half. Water and methylene chloride were added and the organic layer was partitioned, washed with water, dried over magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (ethyl acetate) to give (±)-3-(1-benzylpyrrolidin-3-yl)-5-methyl-2H-isoquinolin-1-one (66.38 g).

1. temperaturethe mixture was cooled to −78° C.
2. stirringAfter stirring at −78° C. for 1 hr
3. additionAfter completion of the dropwise addition
4. temperaturethe reaction mixture was heated to room temperature
5. stirringthe mixture was stirred overnight at room temperature
6. stirringThe mixture was further stirred
7. temperatureunder reflux for 1 hr
8. concentrationthe reaction mixture was concentrated to about half
9. additionWater and methylene chloride were added
10. customthe organic layer was partitioned
11. washwashed with water
12. dry with materialdried over magnesium sulfate
13. concentrationconcentrated
14. customThe obtained residue was purified by column chromatography (ethyl acetate)

ORDレコード

ord-aebbcb9d04be49ad85accc8374f79715

出典データセット

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07812178B2