Sodium hydride → (4-Bromo-benzyl)-(3-fluoro-propyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of compound 138 (286 mg, 1.0 mmol) in anhydrous DMF (3.0 mL) was added sodium hydride (NaH, 60% oil dispersion, 48.0 mg, 1.2 mmol, 1.2 equiv) at 0° C. The resulting mixture was stirred at 0° C. for 30 min before 1-bromo-3-fluoropropane 139 (170 mg, 1.2 mmol, 1.2 equiv) was added. The reaction mixture was subsequently warmed to 50–60° C. and stirred for 24 hours. The reaction mixture was then quenched with H2O (10 mL), and the resulting aqueous solution was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with H2O (10 mL) and saturated aqueous NaCl (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (10–15% EtOAc/hexane gradient elution) to afford bromide 136 (158 mg, 46% yield) as a colorless oil.

Provenance & Evidence