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

HRID 486184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486184
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]2[C:23](=[O:27])[CH2:24][CH2:25][CH2:26][C:15]=12.[CH3:28][C:29]1[N:33]([C:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=[N:31][C:30]=1[CH:53]=[O:54]>O1CCCC1.CCCCCC.O>[OH:54][CH:53]([C:30]1[N:31]=[CH:32][N:33]([C:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:29]=1[CH3:28])[CH:24]1[C:23](=[O:27])[N:16]2[C:17]3[C:22]([C:14]([CH3:13])=[C:15]2[CH2:26][CH2:25]1)=[CH:21][CH:20]=[CH:19][CH:18]=3

Komponenten

8

Edukt 4

HCID 7912DiisopropylamineHCID 1107438710-methyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-oneHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 150519238,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of diisopropylamine (1.89 g) in tetrahydrofuran (30 ml) at -70° C. under a nitrogen atmosphere was added 1.64M n-butyllithium in hexane (11.5 ml). After being stirred at the same temperature for 20 minutes, the mixture was treated with a solution of 8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (3.39 g) in tetrahydrofuran (39 ml) over 15 minutes. The mixture was stirred at -70° C. for 30 minutes, and a solution of 5-methyl-1-trityl-1H-imidazole-4-carbaldehyde (6.0 g) in tetrahydrofuran (75 ml) was added dropwise over 20 minutes. After the mixture was stirred at -70° C. for further 55 minutes, it was diluted with water and extracted with methylene chloride. The organic layer was washed with water twice and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10 -methylpyrido[1,2-a]indol-6(7H)-one. The product was a mixture of two diastereoisomers.

Aufarbeitung

  1. stirringThe mixture was stirred at -70° C. for 30 minutes
  2. stirringAfter the mixture was stirred at -70° C. for further 55 minutes
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water twice
  5. dry with materialbrine, dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f75a26be5f164446b3790d2e3ee1b387
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290785

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