HCID 22262200, compound → (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[3-(2,2,3,3-tetrafluoropropyl)phenyl]propan-1-ol

HRID 1610701Notes

Reaction equation

HRID 1610701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:32])[CH:9]([NH:24]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])[CH:12]=2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[NH2:24][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])[CH:12]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:32]

Participants

3

Reactant 1

HCID 22262200HCID 22262200, compound

Product 1

HCID 22261956(1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[3-(2,2,3,3-tetrafluoropropyl)phenyl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[3-(2,2,3,3-tetrafluoropropyl)benzyl]ethyl]carbamate (2.188 g, 4.762 mmol) and trifluoroacetic acid (10 ml) were stirred at room temperature for 1 hr. The reaction solution was evaporated under reduced pressure, diluted with water, alkalified with potassium carbonate, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and passed through APS-silica gel. The solvent was evaporated under reduced pressure to give the objective substance.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give the objective substance

Sources & evidence

ORD record
ord-765bdb67f69f4863b551f58f1ec17080
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…