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

Participants

Reaction Steps

1,1,1-Triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (3.34 g, 7.87 mmol) was added to a solution of 1-(tert-butoxycarbonyl)-4-(hydroxymethyl)piperidine (1.50 g, 6.97 mmol, from Step A) in CH2Cl2 (45 mL) and the mixture was stirred at rt for 40 min. Ether (100 mL) and 1.3 N aq. NaOH (45 mL) were added and stirring was continued for 15 min. After transfer of the mixture to a separatory funnel, the aqueous layer was extracted with ether (50 mL). The organic layers were washed in succession with 1.3 N aq. NaOH (45 mL) and water (50 mL), dried (Mg2SO4), filtered, and evaporated to give 1.21 g of the title compound as a colorless oil.

Provenance & Evidence