3,5-Bis(benzyloxy)-4-((tert-butyldimethylsilyloxy)methyl)pyridine → 4-((Tert-butyldimethylsilyloxy)methyl)pyridine-3,5-diol

Participants

Reaction Steps

To 3,5-bis(benzyloxy)-4-((tert-butyldimethylsilyloxy)methyl)pyridine (720 mg, 1.66 mmol, 1 eq.) in a mixture of EtOAc/EtOH (5/2, 28 mL) was added Pd/C (400.0 mg). The mixture was charged with H2 (60 psi), stirred at rt for 2 h, filtered, and concentrated to give 4-((tert-butyldimethylsilyloxy)methyl)pyridine-3,5-diol as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 2H), 4.91 (s, 2H), 0.73 (s, 9H), −0.00 (s, 6H). LRMS (M+H) m/z 256.1.

Provenance & Evidence