HCID 58172045, compound → HCID 58172101, compound

Participants

Reaction Steps

5-Benzyloxy-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (170 mg, 0.37 mmol, 1.0 equiv) was dissolved in the mixture of DMF (3 mL) and EtOH (18 mL) and 30 mg of 20% Pd(OH)2 on carbon was added. The reaction was subjected to 40 psi of hydrogen gas in Parr apparatus for 10 h. The catalyst was filtered off over diatomaceous earth and the ethanol was removed on the rotovap. The residue was taken up in EtOAc and washed 3×20 ml, of brine. The organic layer was dried (Na2SO4), filtered, and evaporated. The crude product is a mixture of starting material and product. The crude residue was purified by flash chromatography on silica using 0% EtOAc in hexanes graded to 30% EtOAc in hexanes as the mobile phase to yield 5-hydroxy-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (56 mg, 41%). This material was used without further manipulation.

Provenance & Evidence