Tetrahydrofuran → HCID 178455324, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0 M sodium bistrimethylsilylamide solution in THF (3.3 ml, 3.25 mmol) was added to anhydrous THF (5.0 ml), and the mixture was cooled to −78° C. A solution of benzyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)acetate (1.0 g, 2.76 mmol) in anhydrous THF (10 ml) was added dropwise to the mixture over 20 min. The mixture was stirred at −78° C. for 30 min, and a solution of n-benzyl-benzenesulfonyloxaziridine (860 mg, 3.25 mmol) in anhydrous THF (7 ml) was added dropwise over 30 min. The mixture was stirred at −78° C. for one hr, was quenched with a saturated aqueous ammonium chloride solution, and was extracted with ether. The organic layer was washed with water and saturated brine, was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=93:7) to give the title compound as a yellow oil (650 mg, yield 63%).

Provenance & Evidence