Water → Tert-butyl 3-(4-fluorophenoxy)pyrrolidine-1-carboxylate

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Reaction Steps

Sodium hydride (554 mg, 13.84 mmol) is added to a solution of 4-fluorophenol (1.60 g, 14.20 mmol) in DMF (20 ml) and the mixture is stirred at room temperature for 2 minutes. 3-Methanesulphonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester is added and the mixture heated at 60° C. for 18 hours. Water (50 ml) is then added and the resulting product is extracted using diethyl ether (3×30 ml). The organic extracts are dried (using MgSO4), filtered and evaporated to give a white solid, which is purified using column chromatography over silica gel (ethyl acetate/isohexane 1:9 v/v) to give the title compound.

Provenance & Evidence