Water → 3-(4,4'-Dimethoxytrityloxy)methyl-5-fluoromethylbenzylamine

Participants

Reaction Steps

To a solution of 3-(4,4′-dimethoxytrityloxy)methyl-5-fluoromethylbenzylazide (39) (247 mg, 0.50 mmol) in THF (5.00 mL) were added water (0.20 mL) and then triphenylphosphine (264 mg, 1.01 mmol). The air was evacuated from the reaction system, and then Ar was charged therein. The reaction mixture was stirred for 15 hours at a room temperature. TLC was used to confirm the progress of the reaction. Then, 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 (EtOAc, then EtOAc: MeOH=2:1) to isolate 3-(4,4′-dimethoxytrityloxy)methyl-5-fluoromethylbenzylamine (40) (234 mg, 100%) as a white opaque oil.

Provenance & Evidence