Ammonium Chloride → HCID 23138721, compound

Participants

Reaction Steps

To a solution of (E)-3-{[1-(ethoxycarbonylmethyl)pyrrol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (19.4 g) in ethanol (100 ml) was added sodium borohydride (3.0 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added aqueous ammonium chloride solution, the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed in vacuo. To a solution of the residue in methanol (100 ml) was added potassium carbonate (10.6 g), and the resulting mixture was stirred at room temperature for 15 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 sodium sulfate. The solvent was removed in vacuo to afford the title compound (12.1 g, yield: 64%) as a pale yellow amorphous solid.

Provenance & Evidence