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

To a stirred solution of 5-(3-methoxyphenyl)-2-pyrrolidinone (5.00 g) and tetrahydrofuran (260 ml), at ambient temperature, under nitrogen, was added lithium aluminum hydride (39.3 ml, 1M in tetrahydrofuran). The mixture was heated under reflux for 6 hrs, cooled to ambient temperature, and aqueous tetrahydrofuran was added slowly. The suspension was concentrated, and the residue was dissolved in dilute aqueous sulfuric acid. The solution was made basic (pH 12) by the slow addition of aqueous sodium hydroxide solution. The mixture was extracted with dichloromethane (3 times) and ether (1 time). The combined organic extracts were washed with brine, dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated to give 2-(3-methoxyphenyl)pyrrolidine.

1. temperatureThe mixture was heated
2. temperatureunder reflux for 6 hrs
3. concentrationThe suspension was concentrated
4. dissolutionthe residue was dissolved in dilute aqueous sulfuric acid
5. additionby the slow addition of aqueous sodium hydroxide solution
6. extractionThe mixture was extracted with dichloromethane (3 times) and ether (1 time)
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over anhydrous potassium carbonate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated

ORD record

ord-959fc6477c924b6088cb0a9d98bb0d17

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05338739