[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][N:8]=1.[CH3:14][C:15]1([CH3:26])[CH2:20][C:19](=[O:21])[CH2:18][CH2:17][CH:16]1[C:22]([O:24][CH3:25])=[O:23]>C1(C)C=CC=CC=1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:19]2([OH:21])[CH2:18][CH2:17][CH:16]([C:22]([O:24][CH3:25])=[O:23])[C:15]([CH3:14])([CH3:26])[CH2:20]2)=[N:8][CH:9]=1n-BuLi was added dropwise to a solution of 2,5-dibromopyridine in toluene (30 mL) at −78° C. The reaction mixture was stirred for 1 hour at −78° C., then a solution of methyl 2,2-dimethyl-4-oxocyclohexanecarboxylate in toluene (5 mL) was added. The reaction mixture was warm to room temperature, quenched with saturated aqueous ammonium chloride, extracted with CH2C12 (3×), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford methyl 4-(5-bromopyridin-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate as a colorless oil. MS ESI calc'd for C15H21BrNO3 [M+H]+ 342 and 344. found 342 and 344.
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