HCID 21034891, compound → HCID 22048331, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[C:15]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH:34]([CH2:36][CH3:37])[CH3:35])[CH:28]=2)=[N:14][CH:13]=1)=O)C>O1CCCC1>[CH:34]([O:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][C:15]1[C:16]2[C:21](=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:12]([CH2:10][OH:9])=[CH:13][N:14]=1)([CH2:36][CH3:37])[CH3:35]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of lithium aluminum hydride (309 mg, 7.73 mmol) in anhydrous tetrahydrofuran (15 mL) was added a solution of 1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (2.3 g, 5.44 mmol) in tetrahydrofuran (10 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and the excess lithium aluminum hydride was quenched with addition of water (1 mL), 15% aqueous sodium hydroxide solution (1 mL) and water (3 mL) at 0° C. The mixture was filtered through a Celite® pad and the filtrate was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford [1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-isoquinolin-4-yl]-methanol (2.1, 99% yield). The crude product was used without further purification.
Workup
- customthe excess lithium aluminum hydride was quenched with addition of water (1 mL), 15% aqueous sodium hydroxide solution (1 mL) and water (3 mL) at 0° C
- filtrationThe mixture was filtered through a Celite® pad
- dry with materialthe filtrate was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7e7c07e34e5149ef8a20ca8ed322794b
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067529B2
Reaction notes
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