diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate → Ethyl 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

HRID 1710449노트

반응식

HRID 1710449 반응식
C([O:3][C:4]([C:6]1[N:7]([CH2:20][C:21]#[N:22])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=2)=O)C.[H][H]>CCO.O=[Pt]=O>[CH2:18]([O:17][C:15]([C:10]1[CH:11]=[CH:12][C:13]2[CH:14]=[C:6]3[C:4](=[O:3])[NH:22][CH2:21][CH2:20][N:7]3[C:8]=2[CH:9]=1)=[O:16])[CH3:19]

참가 물질

5

반응물 2

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 68506420Ethyl 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate수율 109.2%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 702Ethanol용매

실험 절차

To 1-cyanomethyl-1H-indole-2,6-dicarboxylic acid diethyl ester (500 mg, 1.66 mmol) in 20 mL of absolute EtOH was added PtO2 (Adams' catalyst). The reaction mixture was hydrogenated at 50 psi of hydrogen overnight. The reaction mixture was filtered through a pad of diatomaceous earth, the solid cake was washed with dichloromethane several times. The solvent was evaporated to dryness to give 468 mg of 1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid ethyl ester as a light yellow solid.

후처리

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washthe solid cake was washed with dichloromethane several times
  3. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-3f22195600214fb980c219b22df37b03
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790712B2

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