Diethyl Ether → tert-Butyl 4-formylpiperidine-1-carboxylate

Participants

Reaction Steps

Periodinane (26.9 g, 63.5 mmol) was added to a solution of 1-tert-butoxycarbonyl-piperidine-4-methanol (10.5 g, 48.8 mmol) in methylene chloride (200 mL) and the mixture was stirred for 90 min. Diethyl ether was added and precipitates were removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 300 mL). The organic layer was washed with 0.5 M NaOH and brine, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 8:2) gave 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (8.5 g, 81%).

Provenance & Evidence