1,1-dimethylethyl(1RS,2SR)-2-(6-fluoropyridin-3-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate → (1RS,2SR)-2-amino-1-(6-fluoropyridin-3-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanol

HRID 1610520Notes

Reaction equation

HRID 1610520 reaction equation
[F:1][C:2]1[N: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]([O: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]([O:17][C:18]([F:22])([F:23])[CH:19]([F:20])[F:21])[CH:12]=1)[CH:8]([C:5]1[CH:6]=[N:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:32]

Participants

3

Reactant 1

HCID 1317252521,1-dimethylethyl(1RS,2SR)-2-(6-fluoropyridin-3-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate

Product 1

HCID 22261670(1RS,2SR)-2-amino-1-(6-fluoropyridin-3-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanolYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1,1-dimethylethyl(1RS,2SR)-2-(6-fluoropyridin-3-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate (1.0 g, 2.16 mmol) was added trifluoroacetic acid (10 ml), and the mixture was stirred at room temperature for 10 min. The reaction solution was concentrated under reduced pressure and 1N aqueous sodium hydroxide solution (10 ml) was added. The mixture was extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give (1RS,2SR)-2-amino-1-(6-fluoropyridin-3-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanol (750 mg, 96%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and 1N aqueous sodium hydroxide solution (10 ml)
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (20 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8a50af2795d748b68475a65f5e7470bd
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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