Sodium Carbonate → 5-(4'-(1-(Methoxyamino)ethyl)-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

Participants

Reaction Steps

Methoxylamine hydrochloride (0.06 g, 0.7 mmol) was added to a stirred solution of potassium t-butoxide (0.06 g, 0.5 mmol) in methanol (10 ml) under argon. After 20 minutes at room temperature, the solution was treated with a solution of 5-(4'-acetyl-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E10, 0.16 g, 0.3 mmole) in methanol (10 ml) and stirred at room temperature for 18 hours, followed by 1 hour heating under reflux. The solution was allowed to cool, treated with 10% Na2CO3 solution (40 ml) and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (0.16 g, 94%).

Provenance & Evidence