Water → methyl 7-bromo-1-(3-methoxypropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 587082노트

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HRID 587082 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.[CH3:17][O:18][CH2:19][CH2:20][CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:21][CH2:20][CH2:19][O:18][CH3:17])[CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 137720Propanal, 3-methoxy-HCID 5049666Sodium triacetoxyborohydrideHCID 22328963Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate

생성물 1

HCID 22328931methyl 7-bromo-1-(3-methoxypropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate수율 93.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.80 g) and 3-methoxypropionaldehyde (1.25 g) in 1,2-dichloroethane (10 ml) was added sodium triacetoxyborohydride (1.81 g) at room temperature, and the mixture was stirred for 24 hours. Water was added to the reaction system, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the resulting residue was separated and purified with column chromatography (ethyl acetate hexane=1:3→1:2) to give methyl 7-bromo-1-(3-methoxypropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (935 mg) as yellow oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe resulting residue was separated
  6. custompurified with column chromatography (ethyl acetate hexane=1:3→1:2)

출처 및 근거

ORD 기록
ord-012377a71bdf41e7b0af5d3ba4d0995f
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936602B1

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