Ethyl trifluoroacetate → 2,2,2-trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]acetamide

HRID 2220594Notes

Reaction equation

HRID 2220594 reaction equation
[CH3:1][C@H:2]([NH2:12])[C@H:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[F:13][C:14]([F:21])([F:20])[C:15](OCC)=[O:16]>C(O)C>[F:13][C:14]([F:21])([F:20])[C:15]([NH:12][C@@H:2]([CH3:1])[C@H:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:16]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 6931143P-Hydroxynorephedrine

Product 1

HCID 866117652,2,2-trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (−)-4-hydroxynorephedrine (90 g) and ethyl trifluoroacetate (96 mL) in ethanol (543 mL) was stirred at room temperature for 4 hrs. The reaction mixture was concentrated in vacuo, and then ethyl acetate and water were added to the residue. The organic layer was separated, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (128 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionethyl acetate and water were added to the residue
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7eaf8629a8664a5a9753d07add479174
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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