Water → tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

HRID 1019676ノート

反応式

HRID 1019676 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br-:19].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:19])[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 962WaterHCID 4460996Boc-3-amino-1,2,3,4-tetrahydroquinolineHCID 21124087Pyridiniumtribromide

生成物 1

HCID 17758659tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate収率 1,863.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of XXIII (2.7 g, 10.9 mmol) in THF was added dropwise a solution of pyridinium tribromide (3.83, 0.41 mmol) in 50 mL of THF at rt. The reaction mixture was stirred for 15 min before 60 mL of water was added into the flask. The aqueous phase was extracted with EtOAc. The combined organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography to give (6-bromo-1,2,3,4-tetrahydro-quinoline-3-yl)-carbamic acid tert-butyl ester XXIV (2.5 g, 70%) as white solid.

後処理

  1. additionwas added into the flask
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washThe combined organic phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography

出典と根拠

ORDレコード
ord-7fdb4c85ec1a48388b723a181969008f
出典データセット
uspto-grants-2014_05
特許番号
US08716285B2

反応ノート

読み込み中…