[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:22])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C1COCC1>[Si:29]([O:28][CH2:27][CH2:26][O:22][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:10]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]To a mixture of (R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (0.1964 g, 0.60 mmol, 1.0 equiv) and 60% NaH in oil (0.753 g, 18.8 mmol, 31 equiv) in THF (15 mL) was added (2-bromoethoxy)-tert-butyldimethylsilane (2.042 g, 8.5 mmol, 14 equiv). The resulting mixture was heated at 80° C. for 19 h and then quenched with water, extracted with EtOAc and dried over Na2SO4. After the solvent was removed, the crude product was used in the next step without further purification.
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