5-(3-Methoxyphenyl)-2-pyrrolidinone → 2-(3-Methoxyphenyl)pyrrolidine

To a solution of 5-(3-methoxyphenyl)-2-pyrrolidinone (7.0 g) in dry tetrahydrofuran (280 ml) was added 1M lithium aluminum hydride in tetrahydrofuran (55 ml) dropwise, at ambient temperature, under nitrogen. Upon completion of the addition, the reaction mixture was heated under reflux for 2 hrs, cooled to ambient temperature, and quenched with 10% aqueous tetrahydrofuran (60 ml) followed by 10% sodium hydroxide solution (50 ml). The suspension was filtered through a pad of celite, and the filter cake was washed with dichloromethane. The combined filtrates were concentrated. The concentrate was dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated to give 6.3 g (96%) of 2-(3-methoxyphenyl)pyrrolidine.

1. customat ambient temperature
2. additionUpon completion of the addition
3. temperaturethe reaction mixture was heated
4. temperatureunder reflux for 2 hrs
5. customquenched with 10% aqueous tetrahydrofuran (60 ml)
6. filtrationThe suspension was filtered through a pad of celite
7. washthe filter cake was washed with dichloromethane
8. concentrationThe combined filtrates were concentrated
9. dry with materialThe concentrate was dried over anhydrous potassium carbonate
10. filtrationfiltered
11. concentrationthe filtrate was concentrated

ORD record

ord-eb603b20280a4048b20c58f8863766f4

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05591856