Potassium Carbonate → 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 49493ノート

反応式

HRID 49493 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:24][CH:25]=[CH:26][CH2:27][CH2:28]Br>CN(C=O)C.CCOCC.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:28][CH:27]=[CH:26][CH2:25][Br:24])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 10657398N-Boc-5-HydroxyindolineHCID 536293111,4-Dibromobut-1-ene

生成物 1

HCID 695150785-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester収率 31.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

514 mg (2.3 mmol) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 12 ml DMF were treated with 830 mg (6 mmol) powdered K2CO3 and 1070 mg (5 mmol) 1,4-dibromobutene. The suspension was stirred at 50° C. for 3 h, cooled to RT, diluted with ether and water. The aqueous phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with hexane/EtOAc 9:1 yielded 270 mg (31%) 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless solid, MS: 368 (MH+, 1Br).

後処理

  1. temperaturecooled to RT
  2. extractionThe aqueous phase was extracted with ether
  3. washthe organic phases were washed with water
  4. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-191c59b28e964af6a3cd91ce94ab1f94
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

反応ノート

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