[H-].C([Al+]CC(C)C)C(C)C.CON(C)[C:14](=[O:29])[C:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:17])[CH3:16].CO.Cl>C1COCC1.CCOCC>[CH3:17][C:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:16])[CH:14]=[O:29]
Diisobutylaluminum hydride (1.77 mL, 1M solution in toluene, 0.708 mmol) was added to a stirred solution of benzyl {2-[methoxy(methyl)amino]-1,1-dimethyl-2-oxoethyl}carbamate (198.5 mg, 0.708 mmol) in dry THF (7.1 mL) at −78° C. under N2. The reaction was stirred at −78° C. for 4 h. MeOH (100 mL) and 1N HCl (250 μL) were added and the reaction was allowed to warm to room temperature. The mixture was diluted with Et2O (50 mL) and washed with 1N HCl (2×50 mL), 50% saturated NaHCO3 (50 mL) and water (50 mL), then dried (MgSO4) and concentrated in vacuo to give benzyl (1,1-dimethyl-2-oxoethyl)carbamate. Rf=0.40 (20% EtOAc in hexanes). LCMS calc.=244.1; found=244.1 (M+Na)+. 1H NMR (500 MHz, CDCl3) δ 9.43 (s, 1H), 7.38-7.30 (m, 5H), 5.34 (s, 1H), 5.09 (s, 2H), 1.37 (s, 6H).
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