S(O)(O)(=O)=O.[NH2:6]O.C([O-])(O)=O.[Na+].[F:13][CH2:14][C:15]([CH2:22][F:23])([CH3:21])[C:16](=[O:20])[CH2:17][C:18]#[N:19].Cl>CO.O>[F:13][CH2:14][C:15]([C:16]1[O:20][N:19]=[C:18]([NH2:6])[CH:17]=1)([CH3:21])[CH2:22][F:23]To a mixture of hydroxylamine sulfate (0.59 g, 3.6 mmol) and NaHCO3 (0.700 g, 8.3 mmol) in MeOH (1 mL) and water (10 mL) was added 5-fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrile (0.483 g, 3 mmol). After heated at 60° C. for 8 hours, to it was added 10% HCl until pH 1. It was heated at 60° C. for 3 hours, basified with saturated NaHCO3, and extracted with CH2Cl2. Extracts were dried over MgSO4 and concentrated under reduced pressure to afford 5-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-3-amine as needles (0.289 g, 55%). 1H NMR (300 MHz, CDCl3) δ 5.76 (s, 1H), 4.59 (q, 2H), 4.50 (q and br, 4H), 1.37 (s, 3H); LC-MS (ESI) m/z 177 (M+H)+.
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