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

HRID 406772Notes

Reaction equation

HRID 406772 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. Yield: 4.04 g (905 of theory); Mass spectrum (ESI−): m/z=214/216 (Br) [m+H]+.

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-66146b30c70a4d7db402106075e5307e
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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