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

HRID 1694906노트

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HRID 1694906 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5245511-Bromo-3-methoxypropaneHCID 666456104-(2-Hydroxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

생성물 1

HCID 666455094-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester수율 70.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-ffe28787a7ca443ab4c23513159bd168
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158790B2

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