HCID 86672462, compound → Tert-butyl 4-(2,2-difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Participants

Reaction Conditions

Reaction Steps

To tert-butyl 4-(2,2-difluoroethyl)-2-((2-oxoethyl)carbamoyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (331 mg, 0.82 mmol) in THF (3 mL) was added Burgess' Salt (486 mg, 2.04 mmol). The reaction mixture was heated at 70° C. for 20 minutes under an atmosphere of nitrogen. The reaction mixture was cooled to room temperature, partitioned between EtOAc and saturated aq. NaHCO3, the layers separated and the aqueous layer was extracted once more with EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give an orange oil. The residue was purified by silica gel column chromatography using 0-30% EtOAc in DCM as eluent to yield tert-butyl 4-(2,2-difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (121 mg, 38%) as an off white foam. ESI-MS m/z calc. 387.2. found 388.3 (M+1)+; Retention time: 1.81 minutes (3 min run).

Provenance & Evidence