Imidazole → 3-(Tert-butyldiphenylsilyloxy)butan-1-amine

Participants

Reaction Steps

To a solution of 2-hydroxybutylamine (4.00 g, 44.87 mmol) in anhydrous DMF (25 mL) was added tert-butyldiphenylsilylchloride (16.9 mL, 66.19 mmol) and imidazole (9.16 g, 13.46 mmol). The reaction mixture was stirred at room temperature for 2 days, then concentrated under reduced pressure, and diluted with CH2Cl2 (150 mL). The organics were washed with 5% aqueous NaHCO3 solution (50 mL), brine (50 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by column chromatography (0 to 100% EtOAc in hexane) to give 3-(tert-butyldiphenylsilyloxy)butan-1-amine (8.00 g, 54%) as a white solid. 1H NMR and MS consistent.

Provenance & Evidence