(6-benzyloxy-1-methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester → [6-hydroxy-1-methyl-1H-indole-3-yl]acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (6-benzyloxy-1-methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (0.68 g, 2.10 mmol) in 1,4-dioxane (12 mL) is added a slurry of Pd/C (10%, 0.25 g). The flask is evacuated and re-filled with N2 three times. The mixture is heated to 100° C. and a solution of sodium hypophosphite, hydrate (5.0 g, 47 mmol) in water (5 mL) is added dropwise. The mixture is stirred at 100° C. for 16 hours and cooled to room temperature. The mixture is filtered through a pad of diatomaceous earth and the filtrate is concentrated under reduced pressure. The residue is purified via silica gel chromatography eluting with 25-50% EtOAc/Hexanes to provide the title compound (0.24 g, 52%). ES/MS m/e 220.0 (M+1), 218.0 (M−1).

Provenance & Evidence