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

HRID 2079779ノート

反応式

HRID 2079779 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-033916b7778a4efba827c8141e8ad27f
出典データセット
uspto-grants-2011_04
特許番号
US07932246B2

反応ノート

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