Trifluoroacetic acid → (2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-en-1-ol

HRID 2075375Notes

Reaction equation

HRID 2075375 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:18]C(=O)OC(C)(C)C)[C@H:4]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)/[CH:5]=[CH:6]/[CH3:7].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:18][C@@H:3]([C@H:4]([C:8]1[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=1)/[CH:5]=[CH:6]/[CH3:7])[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57633996Tert-butyl (2S,3S,E)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)hex-4-en-2-ylcarbamate

Product 1

HCID 57634111(2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-en-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2S,3S,E)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)hex-4-en-2-ylcarbamate (0.10 g, 0.28 mmol) was taken up in 3 mL of DCM. 1 mL of TFA was added. The mixture was stirred for 1 hour. The solvent was removed under reduced pressure, and the residue was taken up in 5 mL of DCM and 5 mL of 5% aq NaOH. The mixture was partitioned, and the aqueous portion was extracted three times with 5 mL of DCM. The combined organic extracts were dried over MgSO4. Filtration and concentration under reduced pressure afforded (2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-en-1-ol, which was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe mixture was partitioned
  3. extractionthe aqueous portion was extracted three times with 5 mL of DCM
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-48d802af970449d88760e1d274b526d9
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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