2-Azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine → 2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

Participants

Reaction Steps

A suspension of 2-azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (2) (0.83 g, 2.98 mmol) and 5% Pd/C(en) (83.0 mg, 10 wt %) in MeOH (20 mL) was vigorously stirred for 5 hours at a room temperature under a hydrogen atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, the catalyst was removed by suction filtration with a kiriyama funnel. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=30:1 to 10:1) to give 2-aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (3) (603 mg, 80%) as a yellow oil.

Provenance & Evidence