Hydroxyamine hydrochloride → (NE)-N-[[3,3-bis(fluoromethyl)-1-hydroxy-2,1-benzoxaborol-5-yl]methylidene]hydroxylamine

HRID 1750828Notes

Reaction equation

HRID 1750828 reaction equation
[F:1][CH2:2][C:3]1([CH2:15][F:16])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH:13]=O)=[CH:12][C:4]1=2.[NH2:17][OH:18].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[F:1][CH2:2][C:3]1([CH2:15][F:16])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11](/[CH:13]=[N:17]/[OH:18])=[CH:12][C:4]1=2

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866850753,3-Bis(fluoromethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde

Product 1

HCID 89572707(NE)-N-[[3,3-bis(fluoromethyl)-1-hydroxy-2,1-benzoxaborol-5-yl]methylidene]hydroxylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3,3-bis(fluoromethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (400 mg, 1.77 mmol) and NH2OH.HCl (148 mg, 2.12 mmol) in THF (25 mL) and H2O (5 mL) at rt was added NaOAc (203 mg, 2.48 mmol). The mixture was stirred at rt overnight, diluted with H2O and extracted with EA (50 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product (440 mg) was used directly in the next step without purification.

Workup

  1. extractionextracted with EA (50 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product (440 mg) was used directly in the next step without purification

Sources & evidence

ORD record
ord-34b8ac48961b49f1b78a0d76597ae4f1
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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