Hexane → 5-(4'-Acetamidomethyl-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (D8, 85 mg, 0.35 mmole) in toluene (10 ml) at room temperature under argon was treated with 2M trimethylaluminium in hexane (0.74 ml, 1.5 mmole). The mixture was stirred for 0.75 h, then treated with a solution of methyl 4'-acetamidomethyl-2'-methylbiphenyl-4-carboxylate (D21, 120 mg, 0.40 mmole) in toluene (5 ml) and heated at 90° C. for 2 h. The solution was allowed to cool, then poured carefully into a stirred slurry of silica gel (10 g) in dichloromethane (30 ml) and stirring continued until the effervescence had ceased. The silica gel slurry was then packed into a chromatography column and eluted with 0-10% MeOH/CH2Cl2 to afford the title compound (85 mg, 48%). This was converted to the oxalate salt, which crystallised form acetone.

Provenance & Evidence