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

HRID 2079780Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-202a00c4c46445dfa5d3ade1992b7694
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932246B2

Reaction notes

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