Water → tert-Butyl 3-methyl-1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-methyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (I-13) (505 mg, 1.88 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (109 mg, 0.188 mmol), palladium(II) acetate (21 mg, 0.094 mmol), potassium carbonate (520 mg, 3.76 mmol), water (102 μl, 5.65 mmol) and commercially available 4-bromofuran-2-one (368 mg, 2.26 mmol) in toluene (13 mL) was degassed and then heated at 60° C. for 16 hours. The mixture was filtered through a pad of CELITE®, and the filter cake was washed with ethyl acetate. The filtrates were concentrated and the residue was purified by column chromatography eluting with 10-100% ethyl acetate/hexane gradient to give the title compound. LC-MS (IE, m/z): 373.3 (M+23)+.

Provenance & Evidence