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Aluminium lithium hydride → HCID 45273676, 화합물

HRID 1716622
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HRID 1716622 반응식
CO[C:3](=O)[NH:4][CH2:5][CH2:6][CH:7]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:19]1[C:20]2[C:16](=[CH:15][C:14]([CH:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][CH2:5][NH:4][CH3:3])=[CH:22][CH:21]=2)[CH:17]=[CH:18]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 59831838HCID 59831838, 화합물

생성물 1

HCID 45273676HCID 45273676, 화합물수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of [3-(1H-indol-5-yl)-3-phenyl-propyl]-carbamic acid methylester X (0.52 g, 1.7 mmol) in THF (35 ml), LiAlH4 (321 mg, 8.4 mmol) was slowly added. The mixture was refluxed for 1.5 hours, cooled to room temperature, and quenched by slow addition of freshly ground Na2SO4.10H2O The mixture was stirred at room temperature for 1 hour, filtered through celite with EtOAc. The filtrate was evaporated and purified via flash chromatography (DCM/MeOH/NH4OH) affording [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine (XI) as an off-white foam (408 mg, 91% yield). The amine compound was dissolved in a Et2O/THF mixture and HCl (2 M in Et2O, 0.772 ml) was added. The precipitate was filtered, washed with Et2O, and dried affording [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine hydrochloride salt (371 mg, 80% yield). MS (M+H) 265.

후처리

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customquenched by slow addition of freshly ground Na2SO4.10H2O The mixture
  3. filtrationfiltered through celite with EtOAc
  4. customThe filtrate was evaporated
  5. custompurified via flash chromatography (DCM/MeOH/NH4OH)

출처 및 근거

ORD 기록
ord-86c66892ea4c4463b7d07a22002d41d5
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803830B2

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