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

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%).

1. extractionThe resulting mixture was extracted twice with ethyl acetate
2. washThe organic layer was washed with saturated brine (15 ml)
3. dry with materialdried over sodium sulfate
4. customevaporated under reduced pressure
5. customThe obtained crude product
6. customwas purified by flash column chromatography

ORD record

ord-4dfd70b17e0843baaa260bb3395e8323

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173824B2