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

HRID 2301077노트

반응식

HRID 2301077 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e361cb1a865548fdbcbbe2bca783fb82
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498251B1

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