Dimethylformamide → HCID 18770930, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1′-carboxymethyl-4-(4-hydroxyphenyl)spiro[2H-1-benzopyran-2,4′-piperidine]-1′-acetate (432 mg, 1 mmol., prepared according to Example 42), sodium hydrogen carbonate (176 mg, 2.1 mmol) in dry N,N-dimethylformamide (25 cm3) was added ethyl iodide (0.088 cm3, 1.1 mmol) and the mixture was heated to 0.80° C. for 2 h. Upon cooling, it was diluted with ethyl acetate (100 cm3) and washed with water (5×100 cm3). The organic solution was then dried over sodium sulfate before the solvent was removed in vacuo. The crude material was then passed through a short pad of silica first with dichloromethane (which was discarded) and then with ethyl acetate. The solvent was removed to afford the desired product (194 mg, 51%).

Provenance & Evidence