Aluminium lithium hydride → HCID 54438845, compound
Reaction equation
C[O:2][C:3]([C:5]1[C:18]2[CH2:17][CH2:16][C@H:15]3[C@@H:10]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:19]([N:14]1[C@@H:15]2[C@H:10]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH2:3][OH:2])[C:18]=3[CH2:17][CH2:16]2)[CH2:11][CH2:12][CH2:13]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of trans-4-benzyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinolin-7-carboxylic acid methyl ester (1.9 g, 5.67 mmol) in 50 mL of dry diethyl ether was cooled to 0° C. Solid lithium aluminum hydride (1.5 g, 39.5 mmol) was then added in small portions. The mixture was stirred for 1 hour at 0° C. The reaction was then terminated by the addition of water (1 mL), 15% sodium hydroxide solution (1 mL) and finally water (3 mL). The resulting mixture was filtered through a pad of Celite, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on a silica column with methanol:dichloromethane (1:19 (v/v)) as eluant. The solvents from the collected fractions containing pure 48 were evaporated yielding 1.5 g (86%) as an oil.
Workup
- customThe reaction was then terminated by the addition of water (1 mL), 15% sodium hydroxide solution (1 mL) and finally water (3 mL)
- filtrationThe resulting mixture was filtered through a pad of Celite
- dry with materialdried (magnesium sulfate)
- customevaporated to dryness
- customThe residue was chromatographed on a silica column with methanol:dichloromethane (1:19 (v/v)) as eluant
- additionThe solvents from the collected fractions containing pure 48
- customwere evaporated
- customyielding 1.5 g (86%) as an oil
Sources & evidence
- ORD record
- ord-05eb9a35a96c4e2098fedcadcd0da025
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05639778
Reaction notes
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