Ammonium Chloride → HCID 9857659, compound

Participants

Reaction Steps

To a solution of zinc chloride (2.0 g, 0.015 mol) and sodium borohydride (1.1 g, 0.029 mol) in t-butyl methyl ether (80 ml) was added dropwise a solution of (4S,5S)-5-hydroxy-4-isopropyl-5-trifluoromethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester (5.0 g, 0.015 mol) obtained in Example 2 in t-butyl methyl ether (20 ml), and the mixture was stirred at room temperature for 15 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution (80 ml), and the mixture was extracted with ethyl acetate (50 ml). The extract was washed with a saturated brine, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and thereto were added each 25 ml of methanol and water, and potassium carbonate (3.1 g), and the mixture was stirred for one hour. The reaction solvent was evaporated under reduced pressure, and thereto was added water (50 ml). The mixture was extracted three times with ethyl acetate (each 50 ml). The extract was washed with a saturated brine, and the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The precipitated crystals were collected by filtration and washed with hexane to give the desired compound (3.0 g, yield: 87%).

Provenance & Evidence