(NE)-N-[1-(1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)ethylidene]hydroxylamine → 6-(1-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037045Notes

Reaction equation

[OH:1][B:2]1[C:6]2[CH:7]=[C:8](/[C:11](=[N:13]/O)/[CH3:12])[CH:9]=[CH:10][C:5]=2[C:4]([CH3:16])([CH3:15])[O:3]1>CC(O)=O.[Zn]>[NH2:13][CH:11]([C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:15])([CH3:16])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)[CH3:12]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of crude compound (E)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanone oxime (0.93 mmol) and zinc dust (260 mg, 4.0 mmol) in AcOH (8 mL) was heated to 40° C. and stirred for 0.5 h. LC-MS showed SM disappeared. The reaction mixture was used for next reaction directly without being purified.

Workup

customThe reaction mixture was used for next reaction directly
customwithout being purified

Sources & evidence

ORD record: ord-b0aac9efda14476a93c47e0d2478591d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546357B2

Reaction notes

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