Hydroxyamine hydrochloride → N-[(3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methylidene]hydroxylamine

HRID 2079779Notes

Reaction equation

HRID 2079779 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH2:9]([N:16]1[CH2:21][CH:20]2[CH:18]([CH:19]2[CH:22]=O)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCO>[CH2:9]([N:16]1[CH2:21][CH:20]2[CH:18]([CH:19]2[CH:22]=[N:2][OH:3])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 200899113-Benzyl-3-azabicyclo[3.1.0]hexane-6-carbaldehyde

Product 1

HCID 71428879N-[(3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methylidene]hydroxylamineYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (1.69 g, 22.84 mmol) and sodium acetate (2.45 g, 29.85 mmol) were added to a stirred solution of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carbaldehyde (1.60 g, 7.96 mmol) in EtOH (100 ml) at r.t. under N2. The reaction was allowed to stir for 16 h. The solvent was then removed in vacuo and the residue partitioned between DCM (100 ml) and aq. K2CO3 (100 ml). The organic layer was separated and the aqueous layer washed with DCM (100 ml). The combined organic layers were dried (MgSO4) and solvent removed in vacuo to give the title compound as a yellow oil (1.57 g, 91%-1:1 mixture of oxime isomers). LCMS purity 85%, m/z 217 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 1.65 (4H, m), 1.86 (1H, m), 2.29 (4H, d, J=9 Hz), 2.50 (1H, m), 2.91 (4H, dd, J=2.4, 9 Hz), 3.57 (4H, s), 6.05 (1H, d, J=9 Hz), 6.96 (1H, d, J=8.1 Hz), 7.21-7.34 (10H, m), 10.28 (1H, s), 10.59 (1H, s).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue partitioned between DCM (100 ml) and aq. K2CO3 (100 ml)
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with DCM (100 ml)
  5. dry with materialThe combined organic layers were dried (MgSO4) and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-033916b7778a4efba827c8141e8ad27f
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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