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-1f91cd3840a741008edee16b2802093a

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05591856