Water → HCID 86618261, compound

Participants

Reaction Steps

To a solution of 7-benzyloxy-1-methanesulfonyl-4-vinyl-1H-indole (1.3 g, 3.9 mmol; Intermediate 84) in dioxane (25 ml), lutidine (900 μl, 7.9 mmol), sodium metaperiodate (3.37 g, 15.8 mmol) (in water (10 ml)) and osmium tetroxide (100 mg, 0.1 mmol) was added (in that order). A precipitate was almost immediately formed, and the mixture was stirred for 1 h at room temperature. Water was added. The precipitate was filtered off, and washed with water. The solid material was extracted with acetonitrile. The acetonitrile-solution was evaporated. The product was purified by strait phase chromatography using Biotage flash-chromatograph 5-40% EtOAc in petroleum ether 40-60° C. Obtained 0.40 mg. MS (ESI+) for C17H15NO4S m/z 330 (M+H)+.

Provenance & Evidence