C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[O:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[Li+].[OH-].CO.C1COCC1>CCOC(C)=O>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([O:11][C:5]2[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=2[C:3]([OH:25])=[O:2])[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]A mixture of methyl-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (3.05 g, 8.64 mmol), 1 M aq LiOH (15 mL, 15 mmol), MeOH (15 mL), and THF (45 mL) was stirred overnight. The reaction was diluted with EtOAc, washed with satd citric acid, dried over MgSO4, concentrated, and triturated with ether to give the desired product as a white solid (2.23 g, 76%).
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