Diisopropylamine → Methyl 2-hydroxy-3-cyclopropyl-3-methylbutanoate

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To a stirred solution of diisopropylamine (4.9 mL, 35 mmol) in dry THF (100 mL) at 0° C. under inert atmosphere was added n-butyllithium (14 mL, 35 mmol) dropwise over a period of 5 min. The solution was cooled to −78 ° C. and methyl 3-cyclopropyl-3-methylbutanoate (5.0 g, 32) was added dropwise over a period of 5 min. The solution was stirred at −78 ° C. for 1 h at which time (+)-camphorsulfonyloxaziridine (9.0 g, 39 mmol) was added all at once. The resulting suspension was stirred at −78 ° C. for 30 min and then allowed to warm to ambient temperature over 30 min. EtOAc (100 mL) and saturated aqueous ammonium chloride (50 mL) were added and the organic layer was separated and washed with water (50 mL), dried (MgSO4), and filtered. The solvents were removed under reduced pressure and the resulting oily solid was stirred in ether (50 mL) for 30 min. The solid was removed by filtration and the filtrate solvent was removed under reduced pressure. The residue was purified by flash column chromatography using a gradient elution of 10% to 14% EtOAc in hexanes to give methyl 2-hydroxy-3-cyclopropyl-3-methylbutanoate as a colorless liquid. TLC Rf=0.4 (12% EtOAc-hexanes); HPLC RT=2.72 min (Method A); 1H NMR 400 MHz, CDCl3, 3.92 ppm ((d, J=7.9 Hz, 1H), 3.79 ppm (s, 3H), 2.79 ppm (d, J=7.9 Hz, 1H), 0.84 ppm (s, 3H), 0.83 ppm (m, 1H), 0.80 ppm (s, 3H), 0.32 ppm (m, 2H), 0.20 ppm (m, 2H)

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