[Br:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C=O)C>[Br:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][Si:18]([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]To a solution (1R*,2R*)-2-bromocyclohexanol (27 g, 0.151 mol) of and imidazole (24.9 g, 0.366 mol) in DMF (500 mL) was added TBSCl (24.9 g, 0.166 mol), the reaction mixture was stirred overnight at rt. Water was added and extracted by EtOAc three times. The combined organic layers were dried, filtered, and concentrated to give ((1R*,2R*)-2-bromocyclohexyloxy)(tert-butyl)dimethylsilane (32 g, 72%). 1H NMR (CDCl3, 400 MHz) δ 0.05-1.05 (d, 6H), 0.90 (s, 9H), 1.20-1.40 (m, 3H), 1.60-1.85 (m, 3H), 1.98-2.10 (m, 1H), 2.25-2.40 (m, 1H), 3.63-3.73 (m, 1H), 3.85-3.97 (m, 1H).
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