Acetone → (2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

反応式

[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[CH:8]=2)[N:3]=1.[BH4-].[Na+].CC(C)=O>CO>[NH2:1][C:2]1[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[CH:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[OH:26])[CH:8]=2)[N:3]=1

参加物

実験手順

To a cooled (ice bath) solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone (0.246 g, 0.581 mmol, prepared as in Example 15, Step 1) in MeOH (10.0 mL) was added sodium tetrahydroborate (0.044 g, 1.162 mmol) in one portion. The reaction mixture was then allowed to warm to RT and stirred for 17 h (overnight). Additional 4 eq of NaBH4 was added and stirred for 7 h until the conversion was completed, determined by LCMS. Acetone was added to quench the excess NaBH4. The resulted solution was concentrated and dried in vacuum to afford crude (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl) (phenyl)methanol as light yellow solid which was used without further purification.