B.C1COCC1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.[CH3:28][O:29][C:30](=[O:44])[CH:31](C)[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([F:41])=[C:37]([CH3:42])[CH:36]=1)=[O:34].[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1>[F:41][C:38]1[CH:39]=[CH:40][C:35]([C@H:33]([OH:34])[CH2:32][CH2:31][C:30]([O:29][CH3:28])=[O:44])=[CH:36][C:37]=1[CH3:42]To a solution of BH3.THF (0.9 mmol) in 20 mL anhydrous THF, was added dropwise at room temperature 158 mL (S)-2-methyl-CBS-oxazaborolidine in toluene and the mixture stirred for 5 min. To this mixture was slowly added methyl 4-(4-fluoro-3-methyl-phenyl)-4-oxo-butyric acid methyl ester (354 mg) in 5 mL THF and stirring continued for 30 min at 25° C. Saturated ammonium chloride (30 mL) was slowly added and the resulting mixture extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×20 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the product isolated by silica gel chromatography to afford 289 mg of the title compound as a colorless oil.
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