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 warmed 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 and 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. customdropwise at ambient temperature
2. additionUpon completion of the addition
3. temperaturethe reaction mixture was warmed
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-6279488ae52a45d285fdcf23d1b637e6

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05554750