Isoamylamine → 7-{2-Fluoro-4-[(3-methyl-butylamino)-methyl]-phenoxy}-2,2-dimethyl-benzo[1,3]dioxin-4-one

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Reaction Steps

4-(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).

Provenance & Evidence