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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
ノート
印刷プレビュー

反応式

HRID 486210 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 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
収率 80.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4fdef91e202d4ee9a6358559bdd1ff60
出典データセット
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05290785

反応ノート

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