C([O:8][C:9](=[O:20])[NH:10][C:11]([CH3:19])([CH2:13][CH:14](O)[CH2:15][CH2:16][OH:17])[CH3:12])C1C=CC=CC=1.[H-].[Na+].C(O)(=O)C>C1COCC1>[OH:17][CH2:16][CH2:15][CH:14]1[O:20][C:9](=[O:8])[NH:10][C:11]([CH3:12])([CH3:19])[CH2:13]1To a cold (0° C.) solution of benzyl(4,6-dihydroxy-2-methylhexan-2-yl)carbamate (460 mg, 1.6 mmol) in 30 mL of anhydrous THF was added sodium hydride (60% dispersion in oil, 128 mg, 3.2 mmol). The reaction was stirred at 0° C. for 15 min then allowed to warm to room temperature and stirred for an additional 4 hours. Acetic acid (ca 3.5 mmol) was added and the mixture was concentrated under reduced pressure. The crude residue was purified by column chromatography (5 to 12% methanol in dichloromethane) to give a white solid (219 mg, 1.26 mmol, 77%). 1H NMR (d6-DMSO, 400 MHz) δ 1.17 (s, 6H), 1.41-1.48 (dd, J=12.3, 13.4 Hz, 1H), 1.64-1.71 (m, 2H), 1.79-1.83 (dt, J=1.8, 13.7 Hz, 1H), 3.49-3.55 (m, 2H), 4.37-4.41 m, 1H), 4.54-4.57 (t, J=5.0 Hz, 1H), 7.2 (br s, 1H). LRMS (ESI/APCI) m/z 174 [M+H]+.
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