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

HRID 1363078ノート

反応式

HRID 1363078 の反応式
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:2]1.[Br-:19].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O.CCOCC>C1COCC1>[C:14]([O:13][C:12](=[O:18])[NH:11][CH:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([Br:19])[CH:6]=2)[NH:1][CH2:2]1)([CH3:15])([CH3:17])[CH3:16]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 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 1A (2.7 g, 10.9 mmol) in THF (50 mL) at RT was added dropwise a solution of pyridinium tribromide (3.83 g, 0.41 mmol) in THF (50 mL). After addition, the reaction mixture was stirred for 15 min, then water (60 mL) and ether (60 mL) added. The aqueous layer was separated, and extracted with EtOAc (2×50 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 50%) in hexane to give the title compound (2.5 g, 70% yield) as a white solid.

後処理

  1. additionAfter addition
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with EtOAc (0 to 50%) in hexane

出典と根拠

ORDレコード
ord-d45b58b72ad84b7aa70b7374ab0c3a26
出典データセット
uspto-grants-2011_02
特許番号
US07884113B2

反応ノート

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