tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → tert-Butyl 4-formylpiperidine-1-carboxylate

Participants

Reaction Steps

To a mixture of lithium aluminum hydride (1M THF solution, 4.4 ml) in ether (4 ml) was added dropwise at −60 C4-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1 g, 3.67 mmols) in ether (6 ml). The reaction mixture was allowed to warm to 0-5 C and then re-cooled to −60 C. Celite was added and reaction was quenched with a solution of KHSO4 (19) in water (3 ml), filtered through Celite. The filtrate was washed with cold 1N HCl, saturated NaHCO3, brine and dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexanes (1:1) to provide title compound (656 mg, 84%). (Org. Prep. Proced. Int., 2000, 32, 96.)

Provenance & Evidence