[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10](OC)=[O:11])=[CH:4][CH:3]=1.[Li]Cl.O.[BH4-].[Na+]>C(O)C.C1COCC1>[C:18]([O:17][C:15](=[O:16])[NH:14][CH:9]([CH2:10][OH:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)([CH3:19])([CH3:21])[CH3:20]To a solution of compound 3e (15 g, 42 mmol) in ethanol (50 mL) and THF (50 mL) was added LiCl.H2O (10 g, 170 mmol) and NaBH4 (6.3 g, 170 mmol) at 0° C. The mixture was stirred at rt overnight. LCMS analysis indicated the total consumption of compound 3e. The precipitate was removed by filtration and the filtrate was concentrated in vacuo to give 3f as a white solid (13 g, 94% yield).
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