Réaction #573366

Équation de réaction

diisopropylamine

n-butyllithium

5-methyl-1-trityl-1H-imidazole-4-carbaldehyde

8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one

→

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

Solvants

tetrahydrofuran

hexane

tetrahydrofuran

water

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred at -70° C. for 30 minutes
2. 2
   workup.STIRRINGAfter the mixture was stirred at -70° C. for further 55 minutes
3. 3
   Extractionextracted with methylene chloride
4. 4
   LavageThe organic layer was washed with water twice
5. 5
   Séchagebrine, dried over anhydrous magnesium sulfate
6. 6
   Autreevaporated in vacuo

Mode opératoire

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.

Source