Water → 4-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694906Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[Cs+].[Cs+].[C:13]([O:17][C:18]([N:20]1[CH2:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])[CH2:22][C:21]1([CH3:35])[CH3:34])=[O:19])([CH3:16])([CH3:15])[CH3:14].O>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:22][C:21]1([CH3:35])[CH3:34])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

450 mg of 3-methoxypropyl bromide (2.94 mmol) and 958 mg of cesium carbonate (2.94 mmol) were added to a solution of 573 mg of 4-(2-hydroxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (10d) (1.96 mmol) in N,N-dimethylformamide (20 ml), and the mixture was stirred at 100° C. for four hours. The reaction mixture was cooled and then water was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=1/1) to obtain 540 mg of the title compound (yield: 70%).

Workup

temperatureThe reaction mixture was cooled
extractionfollowed by extraction with ethyl acetate
washThen, the organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-ffe28787a7ca443ab4c23513159bd168
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158790B2

Reaction notes

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