Ethyl bromoacetate → 4-(1-tert-Butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid ethyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[H-].[Na+]>O1CCCC1>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2)=[CH:15][CH:16]=1)[CH3:27]Participants
5
Procedure
To a solution of 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenol (2.14 g) in tetrahydrofuran (43 l) were added ethyl bromoacetate (1.1 ml) and 60% sodium hydride (368 mg) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, ice water was added and the mixture was extracted with ethyl acetate and washed with 10% aqueous citric acid solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) and dried under reduced pressure to give the title compound (2.605 g).
Workup
- temperaturecooling
- additionwas added
- extractionthe mixture was extracted with ethyl acetate
- washwashed with 10% aqueous citric acid solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-2dc3a6af6251494ab08f78521a6ce33a
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562828B1
Reaction notes
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