Sodium hydride → tert-Butyl 2-oxo-1'-(2,2,2-trifluoroethyl)-spiro[indoline-3,4'-piperidine]-1-acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1′-(2,2,2-trifluoroethyl)-spiro[indoline-3,4′-piperidin]-2-one from Step A (3.30 g, 11.6 mmol) in DMF (10 mL) was added sodium hydride (697 mg of a 60% dispersion in mineral oil, 17.4 mmol) at 0° C. The mixture was stirred at 0° C. for 45 min, then tert-butyl bromoacetate (1.88 mL, 12.8 mmol) was added and stirring was continued at room temperature for 72 h. The reaction mixture was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 80:20, to provide the title compound. MS: m/z=399 (M+1).

Provenance & Evidence