Imidazole → 3-(t-Butyldimethylsilyloxy)methyl-5-fluoromethylbenzylamine

Participants

Reaction Steps

3-Aminomethyl-5-fluoromethylbenzylalcohol (38) (520 mg, 3.07 mmol) and imidazole (923 mg, 13.6 mmol) were dissolved in DMF (15.5 mL). The air was evacuated from the reaction system, and then Ar was charged therein. To the solution was added TBDMSCl (1.03 g, 6.83 mmol), and dissolved. Again the air was evacuated from the reaction system, and then Ar was charged therein. The mixture was stirred for 18 hours at a room temperature. TLC was used to confirm the progress of the reaction. The reaction mixture was extracted with EtOAc. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue was purified by neutral silica gel column chromatography (hexane:EtOAc=1:1) to isolate 3-(t-butyldimethylsilyloxy)methyl-5-fluoromethylbenzylamine (41) (661 mg, 76%) as a colorless oil.

Provenance & Evidence