Ammonium Chloride → (R)-2-Hydroxy-2-(3-isoxazolyl)ethylamine

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To ytterbium(III) chloride in acetonitrile (10 ml) was added 2,6-bis[(4S)-(−)-isopropyl-2-oxazolin-2-yl]pyridine (180 mg) and the solution stirred for 1 h. After cooling to 0° C., 3-isoxazolecarboxaldehyde (580 mg) in acetonitrile (5 ml) followed by TMSCN (0.96 ml) were added. After warming to room temperature overnight, aqueous ammonium chloride solution was added and the product extracted into diethyl ether. The extracts were dried (Na2SO4), the solvent was evaporated off, and the residue taken up in diethyl ether (50 ml). After cooling to 0° C., the solution was added to lithium aluimnium hydride (570 mg) in diethyl ether (10 ml) at 0° C. After 3 h at room temperature, water (0.54 ml), 15% aqueous sodium hydroxide (1.62 ml) and water (0.54 ml) were added sequentially. The mixture was filtered through celite and the solvent was evaporated off to give the sub-title compound as a yellow oil (250 mg, 40% ee).

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