Water → HCID 58443400, compound

Participants

Reaction Steps

A solution of [1-(5-bromo-pyridin-3-yl)-butyl]-carbamic acid tert-butyl ester (6.3 g, 19 mmol) and sodium thiomethoxide (2.7 g, 38 mmol) in anhydrous THF (27 mL) is heated at 70° C. After 2 hours the reaction is cooled to room temperature and water (200 mL) is added. The resultant mixture is extracted with ethyl acetate (3×200 mL). The combined organic layers are combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography on silica gel (eluted with 0 to 60% EtOAc/hexanes) to afford [1-(5-methylsulfanyl-pyridin-3-yl)-butyl]-carbamic acid tert-butyl ester (3.9 g, 68%) as a thick light yellow oil.

Provenance & Evidence