HCID 59424371, compound → HCID 59424399, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(1-benzylpiperidin-4-yl)-3-hydroxy-3-(2-nitrophenyl)propanoate (2.4 mmol, 950 mg) was dissolved in acetic acid (20 mL). Iron (17.7 mmol, 1.0 g) was added to the mixture. Reaction was heated at 85° C. and held with stirring for 1.5 hours. Mixture was cooled to room temperature then diluted with water (30 mL). Solids were decanted off. The aqueous solution was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). The mixture was made basic with aqueous sodium hydroxide. Celite was added to the resulting suspension to create a slurry. Mixture was filtered. Filtrate layers were separated. Aqueous layer was extracted 1× ethyl acetate. Combined organic layers were dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained without further purification as yellow oil in 69% yield. MS m/e (M+H)+=335.3.

Provenance & Evidence