Potassium Carbonate → HCID 68615181, compound

HRID 859204Notes

Reaction equation

[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([F:22])[CH:24]=3)=[CH:18][CH:19]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 62 mg (0.21 mmol) of the crude (RS)-[1-(4-hydroxy-phenyl)-5-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester in 3 ml of 2-butanone is treated with 0.031 ml (0.23 mmol) of 3-fluorobenzyl-bromide and 59 mg (0.42 mmol) of potassium carbonate and the mixture is stirred at 50° C. for 18 h. For the working-up, the reaction mixture is diluted with ethyl acetate and extracted with water. The organic phase is dried over sodium sulfate and evaporated under reduced pressure. For purification, the material obtained is chromatographed on silica gel using a 2:1 mixture of n-hexane and ethyl acetate as the eluent. There are obtained 61 mg (72% of theory) of (RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid tert-butyl ester as a white solid. MS: m/e=401 (M+H)+.

Workup

extractionextracted with water
dry with materialThe organic phase is dried over sodium sulfate
customevaporated under reduced pressure
customFor purification
customthe material obtained
customis chromatographed on silica gel using
additiona 2:1 mixture of n-hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-627ac609efab45caba8b4ff542f609bb
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151111B2

Reaction notes

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