Hydrogen Peroxide → (R)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol

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Reaction Steps

Under a nitrogen atmosphere, a solution of 1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanone (Compound 11: 302.7 mg, 1.116 mmol) in tetrahydrofuran (10 ml) was cooled to −20° C., and lithium tri-sec-butylborohydride (1.02 M in tetrahydrofuran, 1.64 ml, 1.674 mmol) was added dropwise thereto over 15 minutes. After stirring the reaction mixture at the same temperature for 1 hour, methanol (0.75 ml), 3 M aqueous sodium hydroxide solution (1.75 ml) and hydrogen peroxide solution (34.5%, 1.55 ml) were added thereto, and the resulting mixture was stirred in the ice bath for 30 minutes. The resulting mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine (15 ml), dried over sodium sulfate, and evaporated under reduced pressure. The obtained crude product was purified by flash column chromatography to obtain (R)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol (291.1 mg, 95.4%).

Provenance & Evidence