Methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate → Methyl 1-(2-amino-4-formylphenyl)piperidine-4-carboxylate

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Reaction Steps

To a mixture of 10% palladium on carbon (1.67 g, 1.57 mmol) and methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate 58 (3.435 g, 11.8 mmol) was added EtOAc (100 mL). The nitrogen atmosphere was replaced by hydrogen from a double balloon and the reaction mixture was stirred at room temperature for 4 h, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 20% to 60% EtOAc in hexanes) gave methyl 1-(2-amino-4-formylphenyl)piperidine-4-carboxylate 59 (0.488 g, 15.8% yield) as a yellow solid. Mass spectrum: calculated for C14H18N2O3 262.1. found 263.2 (M++1).

Provenance & Evidence