Dimethyl Sulfoxide → Tert-butyl 3-oxopiperidine-1-carboxylate

Participants

Reaction Steps

To a cooled (-65° C.) solution of DMSO (1.42 ml; 20 mmol) in CH2Cl2 (30 ml) was added oxalyl chloride (0.87 ml; 10 mmol). The resulting suspension was stirred for an additional 15 minutes at -65° C., whereupon the product of Step A (2.17 g; 10 mmol) dissolved in 5 ml of CH2Cl2 was added portionwise and the reaction was stirred for an additional 15 minutes at that temperature. Triethylamine (5.56 ml; 40 mmol) was then added dropwise, and the solution was allowed to warm to room temperature, whereupon the reaction was stirred for an additional 1.5 hours. The reaction was quenched with H2O and extracted several times with EtOAc. The combined organic phase was washed with 10% aqueous citric acid, H2O, saturated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 25% EtOAc-hexanes. The fractions containing pure material were combined and concentrated in vacuo to afford 1.87 g of the title compound as a yellow oil.

Provenance & Evidence