Water → 8-Bromo-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 331032ノート

反応式

HRID 331032 の反応式
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=O)[NH:10][C:4]=2[CH:3]=1.B.C1COCC1.O>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuran2 回HCID 50926208-bromo-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

生成物 1

HCID 162444748-Bromo-2,3,4,5-tetrahydro-1H-benzo[b]azepine収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 8-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (500 mg, 2.082 mmol) in THF (20 mL) at RT was added borane-THF complex (1M solution in THF) (5.206 mL, 5.21 mmol). The reaction mixture was refluxed for 3 hours, after which the reaction mixture was cooled in an ice bath before the addition of a further amount of borane-THF complex (1M solution in THF) (7.290 mL, 7.29 mmol). The reaction mixture was once again refluxed overnight. The reaction mixture was cooled in an ice bath before the dropwise addition of water. The aqueous layer was then extracted with diethyl ether (3×25 mL). The organic layers were combined, passed through a hydrophobic frit and concentrated. This residue was purified on silica column eluting with ethyl acetate in cyclohexane (0-15%) to afford the title compound (400 mg). LCMS (A): m/z (M+H)+ 226/228, C10H12BrN requires 225/227 (acidic).

後処理

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. extractionThe aqueous layer was then extracted with diethyl ether (3×25 mL)
  3. concentrationconcentrated
  4. customThis residue was purified on silica column
  5. washeluting with ethyl acetate in cyclohexane (0-15%)

出典と根拠

ORDレコード
ord-eae2ad3fab4b44ddbc40482ddd3a1a00
出典データセット
uspto-grants-2014_11
特許番号
US08877742B2

反応ノート

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