Reacción #49267

Ecuación de reacción

di-tert-butyldicarbonate

dimethylamine

acetic acid

sodium triacetoxyborohydride

5-formylindole

→

5-(dimethylaminomethyl)-1-(tert-butoxycarbonyl)indole

Rendimiento 36.2%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofollowed by purification by slurry

Procedimiento

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%).

Fuente