[CH3:1][C:2]1([CH3:23])[O:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=3[F:22])=[CH:12][C:4]=2[O:3]1.[CH3:24][CH:25]([CH3:29])[CH2:26][CH2:27][NH2:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[K+]>ClCCCl>[F:22][C:15]1[CH:16]=[C:17]([CH2:18][NH:28][CH2:27][CH2:26][CH:25]([CH3:29])[CH3:24])[CH:20]=[CH:21][C:14]=1[O:13][C:11]1[CH:10]=[CH:9][C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:23])([CH3:1])[O:3][C:4]=2[CH:12]=14-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3-fluoro-benzaldehyde (I-1b-1: 30.0 g) and 3-methyl-butylamine (9.15 g) were combined in 1,2-dichloroethane (1.0 L). After stirring at ambient temperature for 1 hour, sodium triacetoxyborohydride (100 g) was added to the solution. After stirring overnight, the reaction mixture was treated with an aqueous 2 N potassium hydroxide solution, the organic phase was separated, dried over magnesium sulfate, filtered, and evaporated to provide the title compound (I-1c-1).
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