Water → Methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587010ノート

反応式

HRID 587010 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][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[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

7

反応物 4

HCID 962WaterHCID 86582-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22328963Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate

生成物 1

HCID 22329284Methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate収率 75.7%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (1.5 g) and 2-methoxybenzaldehyde (3.62 g) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (2.82 g), and the mixture was stirred under nitrogen atmosphere at room temperature for 1 day. Then, water was added to the mixture, and the mixture was extracted-with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1) to give methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.62 g) as yellow oil.

後処理

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-976e414bd5144d8d9613caa3414d721e
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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