C([O:3][C:4](=[O:23])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH3:21])[CH:14]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-].[Li+].[Cl-]>C1COCC1.CO>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:23])=[O:3])[CH2:7][CH2:8]2)=[O:22])=[CH:14][C:15]=1[CH3:21]
To a stirred solution of [4-(4-methoxy-3-methyl-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (0.19 g, 0.60 mmol) in 6 mL of THF and 2 mL of MeOH, was added LiOH (0.13 g, 3.0 mmol in 3 mL of water). After 1.5 hours at ambient temperature the solvent was removed in vacuo, then diluted with 20 mL of water (pH 14). The residue was treated with 12 mL of 1N HCl (pH 4), frozen at −78° C. then lyophilized for 24 hours to yield the title product (0.17 g, 0.54 mmol, 90%) with LiCl salt. MS (ESI) m/z 291.8 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.58 min.
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