Sodium hydride → tert-Butyl [3-(7,8-dimethoxy-2-oxo-1,2-dihydro-3H-3-benzazepin-3-yl)propyl]-methylcarbamate

HRID 420861노트

반응식

HRID 420861 반응식
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[N:9]([CH2:20][CH2:21][CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:10]=[CH:11][C:5]=2[CH:4]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 14194551tert-Butyl (3-chloropropyl)methylcarbamate

생성물 1

HCID 86643007tert-Butyl [3-(7,8-dimethoxy-2-oxo-1,2-dihydro-3H-3-benzazepin-3-yl)propyl]-methylcarbamate수율 137.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
25 °C

실험 절차

Suspend 1.7 g (7.8 mmol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one in 35 ml of DMF and then add 374 mg (9.35 mmol, 1.2 equivalents) of sodium hydride (60% suspension in oil). A clear pale yellow solution is obtained, which is stirred for one hour at 25° C. 1.94 g (9.35 mmol, 1.2 equivalent) of tert-butyl (3-chloropropyl)methylcarbamate dissolved in 10 ml of DMF are then added dropwise. The whole is heated at 50° C. overnight and then the solvent is evaporated to dryness. The residue is taken up in water and extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 4.2 g of an oil is obtained which is purified by flash chromatography on 200 g of silica (eluant=dichloromethane/ethyl acetate:80/20). 2.3 g of the expected product are obtained in the form of a colourless oil.

후처리

  1. customA clear pale yellow solution is obtained
  2. additionare then added dropwise
  3. temperatureThe whole is heated at 50° C. overnight
  4. customthe solvent is evaporated to dryness
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-42615ccfe9fc46af87de3f803fcdde36
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097720B2

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