N-bromobutanimide → 1,1-dimethylethyl 6-bromo-7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 1668585ノート

反応式

HRID 1668585 の反応式
[OH:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C1C(=O)N([Br:30])C(=O)C1>C(Cl)Cl>[Br:30][C:3]1[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=2[CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:2]=1[OH:1]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 589728117-Hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 591505311,1-dimethylethyl 6-bromo-7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate収率 80.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Bromination of 1,1-dimethylethyl 7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (71 mg) was performed with NBS (41 mg) in DCM (2.2 ml) and SiO2 (426 mg) at −15° C. under nitrogen. After 15 minutes SiO2 was filtered off and the solvent was evaporated under reduced pressure. The crude was purified on silica gel (ethyl acetate/petroleum ether, 1/9) obtaining the title compound as a yellow solid (72 mg).

後処理

  1. filtrationAfter 15 minutes SiO2 was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude was purified on silica gel (ethyl acetate/petroleum ether, 1/9)

出典と根拠

ORDレコード
ord-f1a4aad038654991961622ddadc81474
出典データセット
uspto-grants-2011_08
特許番号
US07989444B2

反応ノート

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