Hydrochloric Acid → [4-(5-Ethoxy-2-fluoro-phenyl)-3,6-dimethyl-2-pyridyl]methanol

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Reaction Steps

To a stirred solution of ethyl 4-(5-ethoxy-2-fluoro-phenyl)-3,6-dimethyl-pyridine-2-carboxylate (which may be prepared as described in Description 139) (5.51 g, 17.36 mmol) in absolute ethanol (45 mL) under nitrogen at 25° C., was added sodium borohydride (3.28 g, 86.81 mmol) in portions over 40 min. The resulting mixture was left to stir for another 3 h. It was treated with crushed ice (80 mL) and the pH was carefully adjusted to 7 with the addition of 2M HCl. The reaction mixture was extracted with DCM and the organic layers were washed with brine then collected by passing down a PhaseSep cartridge. Evaporation of the volatiles gave [4-(5-ethoxy-2-fluoro-phenyl)-3,6-dimethyl-2-pyridyl]-methanol (D140) (4.33 g, 15.727 mmol, 90.6% yield) as colourless oil;

Provenance & Evidence