Hydrochloric Acid → HCID 118045989, compound

HRID 595980Notes

Reaction equation

HRID 595980 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([C@H:10]2[CH2:14][O:13]C(C)(C)[N:11]2C(OC(C)(C)C)=O)[CH:6]=[C:7]([F:9])[CH:8]=1.Cl.O1CCOCC1>C(Cl)Cl>[NH2:11][C@@H:10]([C:5]1[CH:6]=[C:7]([F:9])[CH:8]=[C:3]([CH2:2][Cl:1])[CH:4]=1)[CH2:14][OH:13]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 118045222HCID 118045222, compound

Product 1

HCID 118045989HCID 118045989, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-tert-butyl 4-(3-(chloromethyl)-5-fluorophenyl)-2,2-dimethyloxazolidine-3-carboxylate (140 mg, 0.407 mmol) in anhyd DCM (1.357 mL) was added 4 N HCl in Dioxane (1.018 mL, 4.07 mmol) portionwise. The mixture was refluxed at 80° C. overnight. The reaction was not completed. More 4N HCl in dioxane (1. 018 mL, 4.07 mmol) was added, and refluxed for another 24 h. Solvent was removed under reduced vacuum to provide (S)-2-amino-2-(3-(chloromethyl)-5-fluorophenyl)ethanol (70 mg, 84%). LCMS (m/z): 204 (MH+), 0.41 min.

Workup

  1. temperaturerefluxed for another 24 h
  2. customSolvent was removed under reduced vacuum

Sources & evidence

ORD record
ord-80779aebe6cd44b0b583e680a84ec897
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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