Hydrochloric Acid → (S)-2-amino-2-(3-fluoro-5-iodophenyl)ethanol hydrochloride

HRID 596038Notes

Reaction equation

HRID 596038 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12]C(=O)OC(C)(C)C)[CH2:10][OH:11])[CH:5]=[C:6]([I:8])[CH:7]=1.[ClH:20].O1CCOCC1>C(Cl)Cl>[ClH:20].[NH2:12][C@@H:9]([C:4]1[CH:5]=[C:6]([I:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118054565(S)-tert-butyl (1-(3-fluoro-5-iodophenyl)-2-hydroxyethyl)carbamate

Product 1

HCID 118045249(S)-2-amino-2-(3-fluoro-5-iodophenyl)ethanol hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl (1-(3-fluoro-5-iodophenyl)-2-hydroxyethyl)carbamate (2.507 g, 6.58 mmol) was dissolved in DCM (60 mL) and treated with 4 N HCl in dioxane (4.93 mL, 19.73 mmol). The mixture was stirred overnight at room temperature. After the majority of the solvent was evaporated carefully in vacuo, the slurry was triturated with Et2O to afford 1.525 g of a fine white HCl salt of (S)-2-amino-2-(3-fluoro-5-iodophenyl)ethanol (72%), which was isolated by suction filtration. LCMS (m/z): 282.4 (MH+), 0.46 min.

Workup

  1. customAfter the majority of the solvent was evaporated carefully in vacuo
  2. customthe slurry was triturated with Et2O

Sources & evidence

ORD record
ord-364c6127db4b40d18a17a111bef4af86
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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