Sodium Iodide → HCID 18931124, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2,4-dioxo-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (6.9 g, 25.6 mmol), 3-bromo-1,2-propanediol (4.4 g, 28 mmol), sodium iodide (1.5 g, 10 mmol), potassium carbonate (14 g) and DMF (25 mL) was stirred approximately 48 hours at 100° C. Additional 3-bromo-1,2-propanediol (1.5 g, 10 mmol) was added, and the stirring and heating continued for an additional 72 hours. After cooling, the mixture was filtered, the solvent removed from the filtrate under vacuum, and the residue was purified by chromatography eluting with ethyl acetate containing 0.5-1% acetic acid. The fractions containing the product were combined and concentrated, and the residue was treated with ethyl acetate to give tert-butyl 2,4-dioxo-3-(2,3-dihydroxypropyl)-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (1.5 g, 4.4 mmol) as a white solid, m.p. 167°-170° C.

Provenance & Evidence