Water → HCID 18700106, compound

Participants

Reaction Steps

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-trifluoromethylbenzonitrile (1.5 g, 3.7 mmol) from Step 1 above in EtOH (25 mL) was added aqueous NaOH (2.3 g, 57 mmol in 15 mL of water). The mixture was heated to reflux for 48 h. Water was added (50 mL) and the volume was concentrated under reduced pressure to ~50 mL. The mixture was extracted with CH2Cl2 (2×25 mL) and the aqueous phase was acidified to pH 3 by the addition of 5 N aqueous HCl. The mixture was extracted with CH2Cl2 (3×25 mL) and the combined organic extracts were dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-trifluoromethylbenzoic acid as an amorphous solid (HPLC retention time=10.0 min (method A)).

Provenance & Evidence