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

HRID 2079780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079780
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-202a00c4c46445dfa5d3ade1992b7694
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932246B2

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