Cl.[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:10]13-((3-Methoxypropoxy)(phenyl)methyl)piperidine HCl salt (63 mg, 0.212 mmol) was mixed with methyl bromoacetate (20 μL), K2CO3 (75 mg, 2.5 equiv.), and anhydrous DMF (3 mL). The mixture was stirred overnight at rt. LC-MS indicated the reaction was complete. The mixture was diluted with EtOAc and washed with water. The water layer was extracted with EtOAc. The combined organic layers were washed with water and brine, and dried over Na2SO4. After concentration, the residue was purified by flash chromatography on a 4-g silica gel cartridge eluted with a 0-10% methanol in dichloromethane gradient to afford methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetate (19 mg, 27% yield). LC-MS (3 min) tR=1.07 min, m/z 336 (M+1).
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