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Oxalic Acid → 10-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

HRID 486210
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HRID 486210 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]2[C:24](=[O:28])[CH2:25][CH2:26][CH2:27][C:16]=12)[CH3:14].[CH3:29][C:30]1[N:34]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[N:32][C:31]=1[CH:54]=[O:55].C(O)(=O)C(O)=O>O1CCCC1.CCCCCC.O>[CH2:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]2[C:24](=[O:28])[CH:25]([CH:54]([OH:55])[C:31]3[N:32]=[CH:33][N:34]([C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:30]=3[CH3:29])[CH2:26][CH2:27][C:16]=12)[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehydeHCID 1505194510-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-oneHCID 178418339Butyllithium

생성물 1

HCID 1005366010-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one
수율 80.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

To a solution of diisopropylamine (1.85 g) in tetrahydrofuran (15 ml) at -70° C. under a nitrogen atmosphere was added 1.49M butyllithium in hexane (11.5 ml). After being stirred at the same temperature for 35 minutes, the mixture was treated with a solution of 10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (3.2 g) in tetrahydrofuran (20 ml ) over 5 minutes. The mixture was stirred at -70° C. for 40 minutes, and a solution of 5-methyl-1-trityl-1H-imidazol-4-carbaldehyde (5.81 g) in tetrahydrofuran (65 ml) was added dropwise over 30 minutes. After the mixture was stirred at -70° C. for 2 hours and then at room temperature for 1 hour, it was diluted with chilled water, neutralized with aqueous oxalic acid solution, and extracted with methylene chloride three times. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The oil obtained was purified by silica gel column chromatography (1% methanol-chloroform) to give 10-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (6.8 g) as an amorphous powder. The product was a mixture of two diastereoisomers.

후처리

  1. stirringThe mixture was stirred at -70° C. for 40 minutes
  2. stirringAfter the mixture was stirred at -70° C. for 2 hours
  3. waitat room temperature for 1 hour
  4. extractionextracted with methylene chloride three times
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe oil obtained
  9. customwas purified by silica gel column chromatography (1% methanol-chloroform)

출처 및 근거

ORD 기록
ord-4fdef91e202d4ee9a6358559bdd1ff60
출처 데이터셋
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05290785

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