Water → HCID 69480010, compound

Participants

Reaction Steps

(S)-1-(2-Chloro-4-nitro-imidazol-1-yl)-2-methyl-3-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)propan-2-ol prepared in Example 275 (0.492 g, 1.31 mmol) was dissolved in DMF (8 ml). To the solution, sodium hydride (63 mg, 1.57 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 3 hours. To the reaction mixture, water was added. After extraction with ethyl acetate, the organic phase was washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/acetone=4/1) and recrystallized from methylene chloride-ethyl acetate to afford (S)-2-methyl-6-nitro-2-(4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole (0.059 g, yield 13%) as a light yellow solid.

Provenance & Evidence