1-[5-(Benzyloxy)pyridin-2-yl]-4-(methanesulfonyl)piperazine → 6-[4-(Methanesulfonyl)piperazin-1-yl]pyridin-3-ol

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Reaction Steps

1-[5-(benzyloxy)pyridin-2-yl]-4-(methylsulfonyl)piperazine (120 g, 278 mmol) was dissolved in TFA (1.3 L) and the reaction heated to reflux, with stirring, for 3 hours then cooled to room temperature. The TFA was then removed in vacuo and the residue azeotroped with toluene (2×300 mL). The resulting liquor was diluted with DCM (100 mL) and slowly neutralised to pH8 with sat. NaHCO3 (700 mL). The suspension was filtered, washed with water, minimum DCM and ether and dried to give 6-[4-(methylsulfonyl)piperazin-1-yl]pyridin-3-ol as a beige solid (69 g, 270 mol, 97%).

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