[C:1](OC(N1CCC(O)CC1)=O)([CH3:4])([CH3:3])[CH3:2].[C:15](=[O:18])([O-:17])[O-:16].[Cs+].[Cs+].C[N:22](C=O)C>FC1C=CC(C(F)(F)F)=CC=1>[C:15]([O:17][NH2:22])([O:16][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18]Part A: A solution of N-(tert-butyloxycarbonyl)-4-piperidinol (5.00 g, 2.48 mmol), 4-fluorobenzo-trifluoride (3.46 mL, 2.73 mmol), and cesium carbonate (12.1 g, 3.72 mmol) in DMF (60 mL) was heated at 120° C. under N2 for 2 days. The mixture was concentrated, diluted with H2O, and extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried with MgSO4, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexane) provided the BOC-aminoether as a white solid (6.97 g, 81%); Anal. calculated. for C17H22NO3F3: C, 59.12; H, 6.42; N, 4.06. Found: C, 59.29; H, 6.47; N, 3.99.
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