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

HRID 847498
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 847498
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[N:17]12.[CH3:27][C:28]1[N:32]([C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[N:30][C:29]=1[CH:52]=[O:53].C(O)(=O)C(O)=O>O1CCCC1.CCCCCC.O>[OH:53][CH:52]([C:29]1[N:30]=[CH:31][N:32]([C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:28]=1[CH3:27])[CH:23]1[C:22](=[O:26])[N:17]2[C:18]3[C:14]([CH:15]=[C:16]2[CH2:25][CH2:24]1)=[CH:13][CH:21]=[CH:20][CH:19]=3
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 110845538,9-dihydropyrido[1,2-a]indol-6(7H)-oneHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 11756993
8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one
Ausbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of diisopropylamine (658 mg) in tetrahydrofuran (8 ml) at -70° C. under nitrogen atmosphere was added 1.64M butyllithium in hexane (3.96 ml). After being stirred at the same temperature for 20 minutes, the mixture was treated with a solution of 8,9-dihydropyrido[1,2-a]indol-6(7H)-one (1.21 g) in tetrahydrofuran (12 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 (2.29 g) in tetrahydrofuran (20 ml) was added dropwise over 20 minutes. After the mixture was stirred at -70° C. for further 60 minutes and at ambient temperature for 2 hours, it was diluted with water and neutralized with an aqueous solution of oxalic acid. Separated organic layer was washed with 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]pyrido[1,2-a]-indol-6(7H)-one (2.21 g) as an amorphous powder. 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 60 minutes and at ambient temperature for 2 hours
  3. washSeparated organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7c3403708a9f47b8b3c205bd1ee234ac
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05141945

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