1-[2-(Tert-butyldimethylsilyloxymethyl)pyridin-5-yl](1-methyl)ethylamine → (5-(2-Aminopropan-2-yl)pyridin-2-yl)methanol

Participants

Reaction Steps

A solution of 1-[2-(tert-butyldimethylsilyloxymethyl)pyridin-5-yl](1-methyl)ethylamine (1.5 g, 5.35 mmol) in AcOH (15 ml), THF (5 ml) and H2O (5 ml) was heated at 50° C. for 2.5 h. The resultant mixture was concentrated under reduced pressue and then azeotroped with toluene (2×50 ml). The residue was dissolved in CH2Cl2 (15 ml) and MeOH (15 ml) and dry loaded onto silica. Purification by column chromatography on silica, using 10% MeOH/CH2Cl2 containing 1% NH3 solution as eluent, gave the desired alcohol (330 mg, 37%).

Provenance & Evidence