Acetic Acid → 1h-Indole-1-carboxylic acid,5-[(dimethylamino)methyl]-,1,1-dimethylethyl ester

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Reaction Steps

In a similar manner to Step 1 of Reference Example 4, 5-formylindole (5.27 g, 36.3 mmol) was dissolved in acetonitrile (100 mL), and the solution was treated with di-tert-butyldicarbonate (9.17 mL, 39.9 mmol) and DMAP (44.0 mg, 0.360 mmol), then the mixture was treated with 51% aqueous dimethylamine solution (72.0 mL, 724 mmol), acetic acid (41.6 mL, 727 mmol) and sodium triacetoxyborohydride (46.2 g, 218 mmol), followed by purification by slurry using diisopropyl ether to obtain 5-(dimethylaminomethyl)-1-(tert-butoxycarbonyl)indole (3.61 g, yield 36%).

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