Sodium Hydroxide → 3-((R)-1-phenylethylamino)-2-(4-bromophenyl)propan-1-ol
Reaction equation
C([O:4][CH2:5][CH:6]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[CH2:7][NH:8][C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])(=O)C.[OH-].[Na+]>CO>[C:11]1([C@H:9]([NH:8][CH2:7][CH:6]([C:17]2[CH:18]=[CH:19][C:20]([Br:23])=[CH:21][CH:22]=2)[CH2:5][OH:4])[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of diastereopure 3-((R)-1-phenylethylamino)-2-(4-bromophenyl)propyl acetate (2.85 g, 7.57 mmol) in methanol (30.3 ml) was added 1.0N-sodium hydroxide (30.3 ml, 30.3 mmol) at 0° C. The mixture was stirred at room temperature for 3 hours. The mixture was partitioned between saturated ammonium chloride solution and chloroform, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford diastereopure 3-((R)-1-phenylethylamino)-2-(4-bromophenyl)propan-1-ol as white solid (2.40 g, 95%).