Dimethylformamide → Ethyl 3-(1-acetyl-pyrrolidin-2-yl)-4-benzyloxybenzoate

HRID 13263Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C=O.[C:20]([N:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1[OH:39])[C:31]([O:33][CH2:34][CH3:35])=[O:32])(=[O:22])[CH3:21]>[Cl-].[NH4+]>[C:20]([N:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1[O:39][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:31]([O:33][CH2:34][CH3:35])=[O:32])(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 50 °C

Procedure

15 g of potassium carbonate and 6.4 ml of benzyl bromide were added to a dimethylformamide (100 ml) solution of 12.4 g of ethyl 3-(1-acetyl-pyrrolidin-2-yl)-4-hydroxybenzoate, and the reaction liquid was stirred at 50° C. for 1 hour. The reaction liquid was cooled, diluted with aqueous saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1 to 1/2 to 1/3) to obtain the entitled compound as a yellow oily substance.

Workup

customthe reaction liquid
customThe reaction liquid
temperaturewas cooled
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1 to 1/2 to 1/3)
customto obtain the entitled compound as a yellow oily substance

Sources & evidence

ORD record: ord-8077fff77c9c423f871016535b68ea6c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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