HCID 19610221, compound → HCID 19610234, compound
Reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH:4]([C:14](OC)=[O:15])[NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH:4]([CH2:14][OH:15])[NH:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1,2,3,4-tetrahydro-1-methyl-3-methoxycarbonyl-7-methoxyisoquinoline (0.67 g, 2.87 mmol) (described in example 73) in anhydrous tetrahydrofuran (5 mnL) was added dropwise I M solution of lithium aluminium hydride (5.7 nunol) in anhydrous tetrahydrofuran (5.7 mL). The mixture was stirred at rt for 3 hr. The reaction mixture was quenched by a careful addition of 5N NaOH (2 mL). The mixture was stirred at room temperature for 10 min and then filtered and the solid was washed twice with diethylether. The organic filtrates were combined, dried (MgSO4) and concentrated in vacuo to give the desired product as solid foam (0.486 g, 82%): 1H-NMR (CDCl3, δ) 1.48 (d,J=6.31Hz, 3H), 2.46-2.67 (m, 2H), 3.04-3.12 (m, 1H), 3.72 (dd, J=8.4, 11.1 Hz, 1H), 3.72-3.81 (m, 1H), 3.79 (s, 3H), 4.08 (q. J=6.3 Hz, 1H), 6.71-6.75 (m, 2H), 7.02 (d, J =7.8 Hz, 1H): MS showed (M+H) +@ 208.