HCID 19921681, compound → HCID 19921660, compound

Participants

Reaction Steps

A solution of ethyl 3-[3-[(1,1-dimethylethyl)dimethylsilyloxy]prop-1-yl]-2-trimethylsilyl-1H-indole-5-carboxylate (5.0 g, 11.5 mmol), and aqueous 48% HF (1.9 g, 46.0 mmol) in 140 mL of MeCN was stirred at 23° C. for 3.5 h. The solution was quenched with 10% Na2CO3, and the organic material was extracted into ethyl acetate. The organic solution was dried (brine, MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography (50-100% EtOAc-hexanes gradient) of the concentrate yielded the title compound (2 79 g, ) as a white crystalline solid: mp 111°-112° C. Anal. Calcd for C14H17N1O3 : C, 68.00; H, 6.93; N, 5.66. Found: C, 67.94; H, 6.78; N, 5.65.

Provenance & Evidence