Methanol → 3[8(S)-[1(S)-tert.butoxyformamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-1H-pyrrole-2,5-dione

Participants

Reaction Conditions

Reaction Steps

A solution of 1.6 g (2.54 mmol) of 3[8(S)-[1(S)-tert.butoxy formamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-furan-2,5-dione in 20 ml of dry N,N-dimethylformamide was treated with 5.35 ml (25.4 mmol) of hexamethyldisilazane and 0.41 g (12.8 mmol) of methanol. The solution was heated at 50° C. for 3 hours and then treated with an additional 5.35 ml (24.8 mmol) of hexamethyldisilazane and 0.41 g (12.8 mmol) of methanol. After a total of 6 hours the solvent was evaporated under reduced pressure and the residue was re-evaporated with 20 ml of methanol. Flash chromatography of the residue on silica gel using ethyl acetate/hexane (1:2) for the elution gave 1.35 g of 3[8(S)-[1(S)-tert.butoxyformamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-1H-pyrrole-2,5-dione as a red solid of melting point 165°-168° C.

Provenance & Evidence