Methanol → (R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate
反応式
[Si:1]([O:8][CH2:9][C@@H:10]([N:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:25]([O-])=O)[C:16]1=[O:28])[C:11]([O:13][CH3:14])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO>[Pd]>[NH2:25][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[CH:23]=[CH:24][N:15]([C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:11]([O:13][CH3:14])=[O:12])[C:16]2=[O:28]参加物
4
実験手順
A round bottom flask was charged with (R)-methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate (5.5 g, 0.014 mol), methanol (100 mL, 2 mol); palladium, 10% weight on charcoal (0.3 g, 0.003 mol) was added and the reaction stirred under hydrogen atmosphere (1 atm) for 2 h. The reaction was filtered over celite and the solvent removed under reduced pressure and the residue purified by flash chromatography (40 g, 0-10% MeOH/DCM) to yield the product as a yellow sticky mass. MS m/z=377.5 (M+H).