Methanol → 6-(Aminomethyl)-3,3-dimethyl-1,3-dihydro-2,1-benzoxaborol-1-ol

HRID 1037013Notes

Reaction equation

HRID 1037013 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8](/[CH:11]=[N:12]/O)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1.CO>CC(O)=O.[Zn]>[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:15])([CH3:14])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 89573772(NE)-N-[(1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)methylidene]hydroxylamine

Product 1

HCID 866854586-(Aminomethyl)-3,3-dimethyl-1,3-dihydro-2,1-benzoxaborol-1-ol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (E)-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]-oxaborole-6-carbaldehyde oxime (2.7 g, 13.15 mmol) in AcOH (30 mL) at rt was added zinc dust (2.56 g, 39.45 mmol). The reaction mixture was stirred at 40° C. for 4 h under argon. Methanol was added and the mixture was filtered over Celite. The filtrate was concentrated and dissolved in ethyl acetate. The organic layer was washed with water. The water layer was lyophilized to give the crude compound 6-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol as a light yellow solid. It was used in next step without further purification.

Workup

  1. filtrationthe mixture was filtered over Celite
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washThe organic layer was washed with water

Sources & evidence

ORD record
ord-3133d73f3f014748ae1cfcc7f57ed34a
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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