Tetrahydrofuran → 6-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline
Reaction equation
C(OC(=O)CC1C=CC(C#C[C:14]2[CH:23]=[CH:22][C:21]3[CH:20]([N:24]([CH:26]4CC4)C)CC[C:17]([CH3:30])([CH3:29])[C:16]=3[CH:15]=2)=CC=1F)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:39]1CCC[CH2:40]1>>[CH3:40][O:39][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH2:20][NH:24][CH2:26][C:17]2([CH3:29])[CH3:30]Participants
Procedure
A solution of 6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-1-one (Intermediate 17, 3.5 g, 17 mmol) in 100 mL of anhydrous tetrahydrofuran was treated with lithium aluminum hydride (1.3 g, 34.25 mmol) in small portions and the resulting suspension was refluxed for 3 hours under argon. The reaction mixture was then cooled in an ice bath and cautiously quenched with saturated aqueous sodium sulfate solution and the resulting slurry was filtered and the filter-cake washed well with ethyl acetate. The filtrate and washings were evaporated in vacuo to a brown oil which was dissolved in chloroform, the solution was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (3.2 g, ˜100%).
Workup
- temperaturethe resulting suspension was refluxed for 3 hours under argon
- temperatureThe reaction mixture was then cooled in an ice bath
- customcautiously quenched with saturated aqueous sodium sulfate solution
- filtrationthe resulting slurry was filtered
- washthe filter-cake washed well with ethyl acetate
- customThe filtrate and washings were evaporated in vacuo to a brown oil which
- dissolutionwas dissolved in chloroform
- dry with materialthe solution was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-8e324adf81ab4313babc7ba0650d032b
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06369225B1
Reaction notes
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