[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[C:8]([F:16])[CH:7]=1)[CH2:3][CH2:4][OH:5].[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].CCN(C(C)C)C(C)C.C(Cl)Cl>CN(C1C=CN=CC=1)C.O>[Si:21]([O:5][CH2:4][CH2:3][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[C:8]([F:16])[CH:7]=1)[NH2:1])([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]solution of 276 (0.200 g, 0.843 mmol), TBDMS-Cl (0.153 g, 1.01 mmol), DIPEA (0.294 mL, 1.69 mmol), DMAP (0.0103 g, 0.0843 mmol) and DCM (6 mL) was stirred for 1 h at RT and then poured into H2O, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:5) to afford 0.210 g (70.9%) of 3-(tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-amine (278).
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