Benzaldehyde → HCID 91488052, compound

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Reaction Steps

The product of Example 1 (612 mg, 3.0 mmol) was placed in a 25 mL round bottom flask and dissolved in methanol (6 mL). To this solution was added benzaldehyde (0.32 mL, 3.0 mmol) and the mixture was stirred at room temperature for 1 hr. After this time sodium borohydride (170 mg, 4.5 mmol) was added slowly over 10 minutes, and the mixture was allowed to stir for an additional 20 minutes. 15 mL of 1N NaOH was then added to quench the reaction, and the mixture was transferred to a separatory funnel with ethyl acetate. An additional 25 mL of ethyl acetate was added and the organic layer was washed successively with 1N NaOH (3×15 mL), brine (1×15 mL), and then dried over magnesium sulfate, filtered, and evaporated. The product was purified by flash column chromatography with ethyl acetate-hexane (3:7 then 1:1) to yield 3-methyl-but-2-enoic acid [2-(benzylamino-methyl)-phenyl]-amide (839 mg, 95% yield) of a yellow oil. 1H NMR (250 MHz, CDCl3) 10.44 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.39-6.84 (m, 8H), 5.64-5.56 (m, 1H), 3.78 (s, 2H), 3.70 (s, 2H), 2.15 (s, 3H), 1.82 (s, 3H). The amine was then converted to the HCl salt with an excess of 1N HCl in ether to be used in further transformations.

Provenance & Evidence