Ethyl chloroformate → HCID 68958899, compound

Participants

Reaction Steps

To a solution of 1′-benzyl-5-(trifluoromethyl)-3H-spiro[1-benzofuran-2,4′-piperidin] (280 mg, 0.806 mmol) in toluene (3 mL) was added ethylchloroformate (0.093 mL, 0.967 mmol) and the reaction mixture was stirred at reflux temperature overnight, cooled to room temperature, diluted by addition of toluene and washed with aqueous NaHCO3 and water successively. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dissolved in ethanol ((4 mL), aqueous KOH (1.14 g KOH in 1.2 mL of H2O) was added and the reaction mixture was refluxed overnight, cooled to room temperature, ethanol was removed in vacuo. Aqueous layer was extracted with Et2O, combined ether layer was washed with 3N aqueous HCl. Combined acidic layer was made pH 10 by addition of aqueous NaOH. The basic solution was extracted with ethyl acetate. The combined organic layer was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-2% methanol in dichloromethane, 0.2% NH4OH) to give the subtitled compound (156 mg).

Provenance & Evidence