Water → HCID 86609424, compound

Participants

Reaction Steps

To a solution of (E)-3-{[1-(methoxycarbonylmethyl)pyrrol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (12.1 g) in toluene (100 ml) were added thioacetic acid (3.5 ml) and N,N-dimethylformamide dineopentyl acetal (13.7 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3) as the eluent. The amorphous solid obtained was dissolved in methanol (100 ml), and the resulting mixture was stirred at 50° C. for 2 days. The reaction mixture was concentrated in vacuo to afford the title compound (12.8 g, yield: 95%) as a pale yellow amorphous solid.

Provenance & Evidence