Potassium Hydroxide → 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole

Participants

Reaction Conditions

Reaction Steps

A mixture of (-)-3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-(benzenesulfonyl)indole (4.6 g) and powdered potassium hydroxide (3.9 g) in dimethyl sulfoxide (46 ml) were stirred at 70° C. for 1 hour. The resultant mixture was diluted with cold water and extracted twice with a mixture of ethyl acetate-tetrahydrofuran (1:1, V/V). The extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (eluted with 5% methanol in chloroform) to give (-)-3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole (2.9 g) as amorphous powder.

Provenance & Evidence