Dimethylformamide → HCID 18374750, compound

Participants

Reaction Steps

To a 30 ml N,N-dimethylformamide solution of 2.4 g (11.15 mmol) of tert-butyl 4-hydroxymethyl-1-piperidinecarboxylate, 557 mg (60% in oil, 13.9 mmol) of sodium hydride and 1.86 ml (15.6 mmol) of benzyl bromide were added with ice cooling. The mixture was stirred at room temperature for 23 hours. Then, the reaction mixture was diluted with ethyl acetate, and the dilution was washed with water and a saturated aqueous solution of sodium chloride in this order. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain 3.5 g (quantitative) of the captioned compound.

Provenance & Evidence