Sodium Hydroxide → 4-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

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Reaction Steps

4-(N-t-Butoxycarbonyl-4-piperidinyloxy)-2-methoxybenzoic acid methyl ester (1.0 g, 2.7 mmol) from Step 2 was refluxed in EtOH (15 mL) containing aqueous NaOH (5.5 mL of a 1.0 N solution). The solvents were removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (50 mL). The organic phase was washed with water (25 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-t-Butoxycarbonyl-4-piperidinyloxy)-2-methoxy-benzoic acid as an amorphous solid.

Provenance & Evidence