1'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine] → 1'-Methyl-5-(2'-methyl-4'-pyrazinylbiphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

Participants

Reaction Conditions

Reaction Steps

1'-Methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (0.098 g, 0.403 mmol) (D8) was dissolved in toluene (5 ml) and was treated with trimethylaluminium (2.0 M in hexane) (0.810 ml, 1.612 mmol) with stirring under argon. After 0.25 h, a solution of methyl 2'-methyl-4'-pyrazinylbiphenyl-4-carboxylate (D86, 0.136 g, 0.447 mmol) in toluene (5 ml) was added. The reaction mixture was then heated to 80° C. After 2 h, the reaction mixture was allowed to cool and was stirred at room temperature. The reaction mixture was then poured onto a slurry of silica gel (9385~20 ml) in dichloromethane (30 ml). After effervescence had ceased, the slurry was filtered and the filter pad was washed with 20% MeOH/CH2Cl2 (~200 ml). The filtrate was then evaporated under reduced pressure to give a brown oil, which was purified by silica-gel chromatography (9385, 10% MeOH/CH2Cl2 as eluant) to give the title compound as a cream solid (0.091 g, 44%).

Provenance & Evidence