(NE)-N-[(4-fluoro-1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)methylidene]hydroxylamine → 6-(aminomethyl)-4-fluoro-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037140Notes

Reaction equation

[F:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[O:8][B:7]([OH:13])[C:6]=2[CH:5]=[C:4](/[CH:14]=[N:15]/O)[CH:3]=1>C([O-])(=O)C.[Zn]>[NH2:15][CH2:14][C:4]1[CH:3]=[C:2]([F:1])[C:10]2[C:9]([CH3:11])([CH3:12])[O:8][B:7]([OH:13])[C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 42.5 °C

Procedure

To a solution of (E)-4-fluoro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde oxime (1.8 g, 8.57 mmol) in acetate acid (18 mL) at rt was added Zn powder (2.8 g, 42.85 mmol). The reaction mixture was stirred at 40 to 45° C. for 3 h. The mixture was cooled to rt, filtered and concentrated under reduced pressure give crude 6-(aminomethyl)-4-fluoro-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol as white solid. It was used in next step without further purification.

Workup

temperatureThe mixture was cooled to rt
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-bd6ad4e9ce194d08ad67a47ff34a25ca
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546357B2

Reaction notes

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