Methanol → HCID 22645387, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-hexyl-3,4-dimethyl-4-(3-trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 1, 500 mg, 1.19 mmol) in anhydrous N,N-dimethylformamide (6 mL) was added triethylamine (1.7 mL, 12.2 mmol) and anhydrous methanol (1.0 mL, 24.7 mmol). The solution was de-oxygenated by evacuating and flushing with nitrogen five times. Palladium(II) acetate (27 mg, 0.12 mmol) and 1,1 ′-bis(diphenylphosphino)ferrocene (67 mg, 0.12 mmol) were added and the mixture was de-oxygenated again, using the same procedure as before. Carbon monoxide gas was bubbled through the mixture for 5 minutes and it was then stirred under an atmosphere of carbon monoxide and heated at 120° C. overnight. The solvent was removed in vacuo to give a brown oil (0.7 g) which was purified by column chromatography on silica gel (35 g) eluted with a gradient of ethyl acetate:hexane:0.880 ammonia (10:190:1 to 10:90:1 to 25:75:1). This gave the title compound as a yellow oil (250 mg).

Provenance & Evidence