Ethanol → (RS)-2-amino-2-(3-bromo-phenyl)-2-(4-difluoromethoxy-3-methyl-phenyl)-ethanol

HRID 1946916Notes

Reaction equation

HRID 1946916 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:21]([F:23])[F:22])=[C:16]([CH3:24])[CH:15]=3)[CH2:12][O:11]C(=O)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)C.[OH-].[Li+]>O>[NH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:21]([F:22])[F:23])=[C:16]([CH3:24])[CH:15]=1)[CH2:12][OH:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 681534954-(3-Bromo-phenyl)-4-(4-difluoromethoxy-3-methyl-phenyl)-oxazolidin-2-one

Product 1

HCID 68153498(RS)-2-amino-2-(3-bromo-phenyl)-2-(4-difluoromethoxy-3-methyl-phenyl)-ethanolYield 100.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-(3-bromo-phenyl)-4-(4-difluoromethoxy-3-methyl-phenyl)-oxazolidin-2-one (intermediate XVII-2) (5.1 g, 1 eq) in a 9:1-mixture of ethanol and water (50 ml) was added lithium hydroxide (9.2 g, 30 eq). The reaction was stirred at reflux for 3 hours. Then the mixture was allowed to cool to room temperature and concentrated at reduced pressure. The residue was extracted with ethyl acetate (3×20 ml), the combined organic layers were collected, dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel using a 5:1-mixture of cyclohexane and ethyl acetate as the eluent. There were obtained 4.8 g (93% of theory) of the (RS)-2-amino-2-(3-bromo-phenyl)-2-(4-difluoromethoxy-3-methyl-phenyl)-ethanol as a white solid.

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationconcentrated at reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (3×20 ml)
  4. customthe combined organic layers were collected
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel using a 5

Sources & evidence

ORD record
ord-6a5e0c90df5441f78bfef33577b84baa
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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