Potassium Fluoride → 6-(1,4-Dioxaspiro[4.5]decan-8-yl)-5-methylpyridin-3-amine

Participants

Reaction Steps

To a solution of 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine (2.87 g), palladium acetate (314 mg) and potassium fluoride (1.63 g) in tetrahydrofuran (35 ml) and water (16 ml) was slowly added dropwise polymethylhydrosiloxane (PMHS) (1.67 ml) at room temperature with stirring, and then stirred at room temperature for 5 hours. During that time, polymethylhydrosiloxane (PMHS) (1.67 ml) was added twice. After completion of the reaction, water was added thereto, the mixture was extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (1.28 g) as a gray solid. MS (ESI) m/z: 249 (M+H)+.

Provenance & Evidence