Water → HCID 59861752, compound

Participants

Reaction Steps

485 mg of the compound [5-1] was dissolved in a mixed solvent of 18 mL of acetone and 3 mL of water, then 460 mg of 4-methylmorpholine 4-oxide monohydrate and 590 μL of osmium tetroxide (0.1M aqueous solution) were added in that order, and the mixture was stirred overnight at room temperature. 10 mL of 10% aqueous solution of sodium sulfite was added thereto, and after the 30 minutes stirring, the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-0/100), to obtain 351 mg of tert-butyl{(1S)-1-[4-(1,2-dihydroxyethyl) phenyl]ethyl}carbamate [7-1] (hereinafter, referred to as the compound [7-1]) as a colorless oily product.

Provenance & Evidence