Potassium Carbonate → {2-[2-(3-hydroxypropoxy)phenyl]ethyl}-N-methylcarbamic acid tert-butyl ester

HRID 366156

反応式

HRID 366156 の反応式
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH2:28][OH:29]>CN(C)C=O.C(OCC)(=O)C.O.[Cl-].[Cs+]>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:26][CH2:27][CH2:28][OH:29])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 10848357tert-butyl N-[2-(2-hydroxyphenyl)ethyl]-N-methylcarbamate

生成物 1

HCID 20677517{2-[2-(3-hydroxypropoxy)phenyl]ethyl}-N-methylcarbamic acid tert-butyl ester収率 70.2%

試薬・触媒・溶媒 4

HCID 24293Cesium Chloride触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

N-(2-(2-Hydroxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (702 mg, 2.79 mmol) was dissolved in N,N-dimethylformamide (6 ml). Potassium carbonate (1.93 g, 13.97 mmol) and cesium chloride (24 mg, 0.14 mmol) were added. 3-bromo-1-propanol (0.28 ml, 3.07 mmol) was added. The reaction mixture was stirred at 80° C. for 16 h. It was cooled to room temperature and diluted with ethyl acetate (75 ml) and water (75 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with a 10% aqueous solution of sodium hydrogen sulfate solution (70 ml) and a saturated aqueous solution of sodium hydrogen carbonate (70 ml). They were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using ethyl acetate/heptane (1:1) as eluent, to give 606 mg of {2-[2-(3-hydroxypropoxy)phenyl]ethyl}-N-methylcarbamic acid tert-butyl ester.

後処理

  1. temperatureIt was cooled to room temperature
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  4. washThe combined organic layers were washed with a 10% aqueous solution of sodium hydrogen sulfate solution (70 ml)
  5. dry with materialThey were dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customThe crude product was purified by flash chromatography on silica (80 g)

出典と根拠

ORDレコード
ord-b1034021d1a2406aa060b9a7ab64b2f6
出典データセット
uspto-grants-2000_10
特許番号
US06127354

関連ノート

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