Water → HCID 19988990, compound

HRID 973702Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:10]2[CH2:14][N:13]([Si](C(C)(C)C)(C)C)[C:12](=[O:22])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([Li])CCC.[C:28]1(=[O:33])[CH2:32][CH2:31][CH2:30][CH2:29]1.O>O1CCCC1.CCCCCC>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([CH:10]2[CH2:14][NH:13][C:12](=[O:22])[CH2:11]2)=[CH:3][C:2]=1[C:28]1([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperatureagain cooled to -70° C
temperatureto warm gradually to 0° C.
stirringstirred at this temperature for one hour
customthe mixture is evaporated
customchromatographed over silica gel with methylene chloride

Sources & evidence

ORD record: ord-1087ad08676b4a9e819925ce2c7d3fef
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05064854

Reaction notes

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