Hydrochloric Acid → (βS)-β-Amino-3-fluoro-5-(fluoromethyl)benzeneethanol

HRID 595987Notes

Reaction equation

HRID 595987 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:11][OH:12])[CH:5]=[C:6]([CH2:8][F:9])[CH:7]=1.Cl>C(Cl)Cl>[NH2:13][C@@H:10]([C:4]1[CH:5]=[C:6]([CH2:8][F:9])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734611HCID 131734611, compound

Product 1

HCID 118045996(βS)-β-Amino-3-fluoro-5-(fluoromethyl)benzeneethanolYield 118.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl (1-(3-fluoro-5-(fluoromethyl)phenyl)-2-hydroxyethyl)carbamate (220 mg, 0.766 mmol) in DCM (2.5 mL), HCl (4M in dioxane) (1.9 mL 7.66 mmol) was added at room temperature, the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was then concentrated to dryness. The residue was recrystallized from DCM and heptane. The solid was filtered and air dry to yield (S)-2-amino-2-(3-fluoro-5-(fluoromethyl)phenyl)ethanol (145 mg, 0.908 mmol, 100% yield) HCl salt as white solid. LCMS (m/z): 188.2 (MH+), 0.32 min.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. customThe residue was recrystallized from DCM and heptane
  3. filtrationThe solid was filtered
  4. customair dry

Sources & evidence

ORD record
ord-1ab00ffc0a044f58a132d8cfd6ee8319
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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