Water → (E,1R,3aR,7aS)-4-(bromomethylene)-octahydro-1-{(R)-1-hydroxyethyl}-7a-methyl-1H-indene-1-ol

Participants

Reaction Steps

To a mixture of (1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene (Compound 21: 19.2 mg, 0.07524 mmol), methanesulfonamide (21.5 mg, 0.2257 mmol) and AD-mix-α (105 mg), t-butanol (0.4 ml) and water (0.4 ml) were added, and the reaction mixture was stirred at room temperature for 48 hours. Sodium sulfite (113 mg) was added thereto and the resulting mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added thereto, and the resulting mixture was extracted 3 times with ethyl acetate. The organic layer was washed with 2 M aqueous potassium hydroxide solution (1 ml) and saturated brine (2.5 ml), and dried over sodium sulfate, followed by evaporation under reduced pressure. The obtained crude product (23.2 mg) was purified by flash column chromatography to obtain (E,1R,3aR,7aS)-4-(bromomethylene)-octahydro-1-{(R)-1-hydroxyethyl}-7a-methyl-1H-indene-1-ol (18.6 mg, 85.3%).

Provenance & Evidence