Aluminium lithium hydride → 3-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenol
Reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[CH3:13])[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Procedure
3-Hexyl-6-(3-hydroxyphenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 84, 0.34 g, 1.2 mmol) was dissolved in tetrahydrofuran (10 ml). Lithium aluminium hydride (1M in diethyl ether, 1.5 ml, 1.5 mmol) was added under nitrogen and the reaction mixture was stirred for 1 h, before adding more lithium aluminium hydride (1M in diethyl ether, 3.0 ml, 3.0 mmol) and stirring the reaction mixture for 16 h. The reaction mixture was quenched by the addition of aqueous sodium hydroxide solution (1M, 50 ml) and the product was extracted with dichloromethane (150 ml). The organic extracts were dried (Na2SO4) and concentrated in vacuo to give a brown waxy solid. The product was purified by chromatography on silica gel, (20 g) eluting with ethyl acetate to give the pure product as a yellow solid (0.17 g, 51%).
Workup
- stirringstirring the reaction mixture for 16 h
- customThe reaction mixture was quenched by the addition of aqueous sodium hydroxide solution (1M, 50 ml)
- extractionthe product was extracted with dichloromethane (150 ml)
- dry with materialThe organic extracts were dried (Na2SO4)
- concentrationconcentrated in vacuo
- customto give a brown waxy solid
- customThe product was purified by chromatography on silica gel, (20 g)
- washeluting with ethyl acetate
Sources & evidence
- ORD record
- ord-0dafa7f5229540d29472f63b4fcc7152
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049444B2
Reaction notes
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