Potassium Iodide → HCID 86659834, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl hexyl[6-(hydroxymethyl)pyridin-2-yl]carbamate (2.52 g, 8.18 mmol) in acetonitrile (50 mL) was added N,N-diisopropylethylamine (1.59 g, 12.2 mmol). The solution was cooled to 0° C., then methanesulfonyl chloride (1.12 g, 9.81 mmol) was slowly added. After stirring at room temperature for 6 h, N-hydroxyphthalimide (1.46 g, 8.96 mmol), cesium carbonate (5.58 g, 17.1 mmol) and potassium iodide (135 mg, 0.81 mmol) were sequentially added, followed by acetonitrile (10 mL). The heterogenous mixture was stirred at room temperature for 20 h, then N-hydroxyphthalimide (0.33 g, 2.0 mmol) was added and the mixture was stirred at 50° C. for 7 h. The cooled reaction mixture was filtered and the filtrate was concentrated in vacuo. The oily residue was dissolved in ethyl acetate (200 mL), washed with water (100 mL), the organic layer was dried (MgSO4) and concentrated in vacuo. Purification on silica gel afforded tert-butyl (6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)hexylcarbamate as a yellow oil [2.107 g, yield 57%; HPLC/MS: m/z=454 (M+H); log P(HCOOH)=5.48].

Provenance & Evidence