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

HRID 587082ノート

反応式

HRID 587082 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-012377a71bdf41e7b0af5d3ba4d0995f
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

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