Sodium Hydroxide → 3-((R)-1-phenylethylamino)-2-(4-bromophenyl)propan-1-ol

HRID 515461Notes

Reaction equation

HRID 515461 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672824433-((R)-1-phenylethylamino)-2-(4-bromophenyl)propyl acetate

Product 1

HCID 672813523-((R)-1-phenylethylamino)-2-(4-bromophenyl)propan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. customThe mixture was partitioned between saturated ammonium chloride solution and chloroform
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a0d41684a1054f0a8f16bf19db0fab08
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

Loading…