Water → HCID 19988990, compound

Participants

Reaction Conditions

Reaction Steps

2.2 g (0.7 mmol) of 4-(3-bromo-4-methoxy-phenyl)-1-tert-butyldimethylsilylpyrrolidin-2-one in 30 ml of absolute tetrahydrofuran is combined at -70° C. with 8.2 ml (0.7 ml) of a butyllithium solution in hexane. The mixture is allowed to warm up to 0° C., agitated at this temperature for 10 minutes, and again cooled to -70° C. Then a solution of 0.48 g of cyclopentanone in 10 ml of tetrahydrofuran is added dropwise thereto, the mixture is allowed to warm gradually to 0° C., and stirred at this temperature for one hour. After addition of 0.1 ml of water, the mixture is evaporated and chromatographed over silica gel with methylene chloride:acetone=1:1 as the eluent. After repeating chromatography of the corresponding fractions over silica gel with methylene chloride:ethanol=10:1 as the eluent, 110 mg of 4-[4-methoxy-3-(1-hydroxycyclopent-1-yl)phenyl]pyrrolidin-2-one is obtained as an oil.

Provenance & Evidence