Aluminium lithium hydride → (3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanamine

HRID 2079780ノート

反応式

HRID 2079780 の反応式
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH:14]=[N:15]O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH2:14][NH2:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 71428879N-[(3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methylidene]hydroxylamine

生成物 1

HCID 20090019(3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanamine収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A solution of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carbaldehyde oxime (1.57 g, 7.27 mmol) in THF (75 ml) was cooled to 0° C. under N2 and LiAlH4 (965 mg, 25.44 mmol) was added. The reaction was heated to 60° C. for 16 h and then cooled to 0° C. It was quenched with a mixture of H2O (3 ml) and sat. aq. sodium potassium tartrate (1 ml) and the resulting suspension stirred for 30 min. MgSO4 was added and the mixture filtered through celite. The filtrate was then concentrated in vacuo to give the title compound as a light yellow oil (1.35 g, 93%). LCMS purity 80%, m/z 203 [M+H]+, 1H NMR (300 MHz, CDCl3) δ: 1.21 (4H, m), 1.41 (1H, m), 2.36 (2H, d, J=8.7 Hz), 2.52 (2H, d, J=7.2 Hz), 2.97 (2H, d, J=8.7 Hz), 3.54 (2H, s), 7.20-7.36 (5H).

後処理

  1. temperaturecooled to 0° C
  2. customIt was quenched with a mixture of H2O (3 ml) and sat. aq. sodium potassium tartrate (1 ml)
  3. additionMgSO4 was added
  4. filtrationthe mixture filtered through celite
  5. concentrationThe filtrate was then concentrated in vacuo

出典と根拠

ORDレコード
ord-202a00c4c46445dfa5d3ade1992b7694
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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