Acetyl chloride → N-[1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxopyrrolidin-3-yl]acetamide

HRID 859205Notes

Reaction equation

Cl.[NH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][CH:9]=2)[C:5](=[O:23])[CH2:4]1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32].[OH-].[NH4+]>ClCCl>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([N:6]2[C:5](=[O:23])[CH2:4][CH:3]([NH:2][C:31](=[O:33])[CH3:32])[CH2:7]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 25 mg (0.07 mmol) of (RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride in 1 ml of dichloromethane is treated with 22 μl (0.16 mmol) of triethylamine and cooled to 0° C. To this solution, 6 μl (0.08 mmol) of acetylchloride are added and stirring at 0° C. is continued for 30 min. For the working-up, the reaction mixture is treated with 2 ml of ammonium hydroxide solution, the organic phase separated, thereafter dried over sodium sulfate and evaporated under reduced pressure. For purification, the material obtained is chromatographed on silica gel using a 95:5 mixture of dichloromethane and methanol as the eluent. There are obtained 20 mg (78% of theory) of (RS)-N-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-acetamide as a white solid. MS: m/e=343 (M+H)+.

Workup

customthe organic phase separated
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customFor purification
customthe material obtained
customis chromatographed on silica gel using
additiona 95:5 mixture of dichloromethane and methanol as the eluent

Sources & evidence

ORD record: ord-75d714352253457bbc316bb6f8e816d2
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151111B2

Reaction notes

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