Hydrochloric Acid → (S)-1-(4-Bromo-2-methyl-phenyl)-ethylamine

HRID 1640856Notes

Reaction equation

HRID 1640856 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][S@@](C(C)(C)C)=O)[CH3:10])=[C:5]([CH3:18])[CH:4]=1>C(OCC)(=O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH2:11])[CH3:10])=[C:5]([CH3:18])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58102376(R)-2-methyl-propane-2-sulfinic acid [(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]amide

Product 1

HCID 58102386(S)-1-(4-Bromo-2-methyl-phenyl)-ethylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrochloric acid (4 mol/L in 1,4-dioxane, 46 mL) was added to a solution of (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]-amide (crude from Step 2, 8.85 g, ca. 75% pure) in ethyl acetate (80 mL) at room temperature. The solution was stirred at room temperature for 1 h and then concentrated. The residue was taken up in water and the resulting mixture was washed with diethyl ether. The aqueous phase was basified using aqueous 1 M NaOH solution and extracted with dichloromethane. The combined extracts were washed with brine, dried (MgSO4), and concentrated to afford the title compound.

Workup

  1. concentrationconcentrated
  2. washthe resulting mixture was washed with diethyl ether
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d3b14d1020f412ea85d393d93064263
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

Loading…