HCID 67147254, compound → HCID 11992238, compound

Participants

Reaction Steps

The crude 1-(2-acetyl-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-yl)cyclohexanecarbonitrile 8a was dissolved in anhydrous tetrahydrofuran (1.0 mL) and treated with methylmagnesium bromide (1.0 mL 1.0 M solution in butyl ether, 1.0 mmol). The vial was flushed with nitrogen and stirred at room temperature for 3 hours. The reaction was diluted with ethyl acetate (5.0 mL), quenched with saturated aqueous ammonium chloride (1.0 mL) and stirred overnight at room temperature. The layers were separated, the organic layer concentrated under reduced pressure and purified by reverse-phase HPLC (1-25% CH3CN—H2O gradient, with 0.05% TFA, 15 min) to provide 1-(1′-(1-methylcyclohexyl) -1H-spiro[isoquinoline-4,4′-piperidine]-2(3H)-yl)ethanone. LC/MS m/z [M+H]+ 341.2 retention time 1.83 min (10-99% CH3CN—H2O gradient, with 0.05% TFA, 5 min).

Provenance & Evidence