HCID 59424371, compound → HCID 59424399, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(1-benzylpiperidin-4-yl)-3-hydroxy-3-(2-nitrophenyl)propanoate (950 mg, 2.4 mmol) was dissolved in acetic acid (20 mL). Iron(0) (1.0 g, 17.7 mmol) was added to the mixture. The reaction was heated at 85° C. and held with stirring for 1.5 h. The mixture was cooled to room temperature and diluted with water (30 mL). The liquid was decanted away from the solids. The aqueous solution was concentrated in vacuo. The 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 which was in turn was filtered. The filtrate layers were separated. The aqueous layer was extracted with ethyl acetate. Combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The title compound was obtained without further purification as yellow oil in 69% yield. Mass spec.: 335.3 (MH)+.

Provenance & Evidence