Trifluoroacetic acid → 2-Amino-2-[3-(trifluoromethyl)phenyl]ethanol trifluoroacetate

HRID 220646Notes

Reaction equation

HRID 220646 reaction equation
[OH:1][CH2:2][CH:3]([NH:14]C(=O)OC(C)(C)C)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25]>ClCCl>[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].[NH2:14][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59536913HCID 59536913, compound

Product 1

HCID 866466322-Amino-2-[3-(trifluoromethyl)phenyl]ethanol trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Of the compound from Example 59A, 277 mg (0.91 mmol) were dissolved in 10 ml of dichloromethane and admixed at 0° C. with 0.7 ml (9.1 mmol) of trifluoroacetic acid, then stirred at room temperature for 1 hour. The mixture was concentrated on a rotary evaporator. The crude product was taken up in 20 ml of toluene and again concentrated on a rotary evaporator under reduced pressure. The crude product was purified by preparative HPLC [Method 19]. This gave 124 mg (43% of theory) of the target compound.

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. concentrationagain concentrated on a rotary evaporator under reduced pressure
  3. customThe crude product was purified by preparative HPLC [Method 19]

Sources & evidence

ORD record
ord-c0ffab55126b45358bb91d685deb55f2
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

Loading…