Trifluoroacetic acid → 3-(8-Aza-bicyclo[3.2.1]oct-2-en-3-yl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

To 1.25 g (2.74 mmol) tert-butyl-3-{1-[tert-butyl(dimethyl)silyl]-1H-indol-3-yl}-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate in 25 mL CH2Cl2 is added 6 mL of TFA. After stirring at 23° C. for 45 min, the reaction mixture is poured into sat. aqueous NaHCO3 (300 mL) and extracted with 3×50 mL CH2Cl2. The combined organics are washed with 1×100 mL H2O, 1×100 mL of brine, dried over Na2SO4, filtered and evaporated to give 603 mg (2.24 mmol, an 82% yield) of the title compound as a yellow/orange oil. MS (ES) m/z 269 (MH)+.

Provenance & Evidence