Sodium borohydride → HCID 59563789, compound
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:39])[CH:13]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:25][CH:24]=3)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[BH4-].[Na+]>CCO>[OH:38][CH:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH:13]([C:12]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[CH:1]=[N:2][CH:3]=[CH:4]3)=[O:39])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[CH:28][CH:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-(2-oxo-2-phenylethoxy)phenyl)propylcarbamate (E275) in EtOH was added NaBH4 and the solution was stirred for 20 min at room temperature. The mixture was then poured into NaHCO3(sat) and extracted with CH2Cl2. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 5% MeOH/CH2Cl2) gave pure tert-butyl 2-(4-(2-hydroxy-2-phenylethoxy)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E276).