[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1.[NH2:15][OH:16].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[N:15][OH:16])=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1
To a mixture of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (560 mg, 2.95 mmol) and NH2OH.HCl (246 mg, 3.54 mmol) in THF (6 mL) and H2O (1.5 mL) at rt was added NaOAc (339 mg, 4.13 mmol). The reaction mixture was stirred at rt for 16 h, diluted with H2O and extracted with EA (10 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product (620 mg, 100% yield) as a white solid.
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