Aluminium lithium hydride → (R)-Tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Reaction equation
CON(C)[C:4]([C@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][N:7]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:4]([C@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][N:7]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
7.4 g of tert-butyl (3R)-3-{[methoxy(methyl)-amino]carbonyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate are dissolved in 31 ml of diethyl ether under N2. The reaction medium is placed at 0° C. and 0.98 g of lithium aluminium hydride is carefully added. The mixture is stirred at 0° C. for 45 min. After hydrolysis with an aqueous potassium sulphate solution, extraction is carried out with diethyl ether until the aqueous phase is completely depleted. The organic phases are washed with a 3N aqueous hydrochloric acid solution, with a saturated aqueous sodium hydrogen carbonate solution, then with H2O, and finally with a saturated aqueous sodium chloride solution. Drying over MgSO4 and concentration to dryness are carried out. 3.5 g of tert-butyl (3R)-3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate are obtained, which product is subsequently used as it is.
Workup
- customis placed at 0° C.
- customAfter hydrolysis
- extractionwith an aqueous potassium sulphate solution, extraction
- washThe organic phases are washed with a 3N aqueous hydrochloric acid solution, with a saturated aqueous sodium hydrogen carbonate solution
- dry with materialDrying over MgSO4 and concentration to dryness
Sources & evidence
- ORD record
- ord-2ad90f2d7ef24cfead33b144fd9d7f83
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569582B2
Reaction notes
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