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

HRID 2079780노트

반응식

HRID 2079780 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-202a00c4c46445dfa5d3ade1992b7694
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932246B2

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