Methyl iodide → tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

HRID 2301077ノート

反応式

HRID 2301077 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:23]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:23])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

生成物 1

HCID 10989795tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate収率 63.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 66 mg (1.65 mmol) portion of sodium hydride was added to 10 ml of DMF solution containing 300 mg (1.10 mmol) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and stirred at room temperature for 30 minutes, and then 103 μl (1.65 mmol) of methyl iodide were added thereto and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the resulting oil was purified by a silica gel column chromatography (60 cc; elution by ethyl acetate-hexane=1:5) to obtain 200 mg of the title compound (63% in yield).

後処理

  1. stirringstirred overnight at room temperature
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was removed by evaporation under a reduced pressure
  6. customthe resulting oil was purified by a silica gel column chromatography (60 cc; elution by ethyl acetate-hexane=1:5)

出典と根拠

ORDレコード
ord-e361cb1a865548fdbcbbe2bca783fb82
出典データセット
uspto-grants-2002_12
特許番号
US06498251B1

反応ノート

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