Trifluoroacetic acid → HCID 16244194, compound

HRID 646720Notes

Reaction equation

HRID 646720 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([NH:12]C(=O)OC(C)(C)C)[CH:6]2[OH:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:12][CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[CH:6]1[OH:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86607841HCID 86607841, compound

Product 1

HCID 16244194HCID 16244194, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (4-fluoro-1-hydroxy-2,3-dihydro-1H-inden-2-yl)carbamate (0.30 g, 1.1 mmol) in CH2Cl2 (10 mL) was added TFA (1 mL), and the solution was heated to reflux. The solution was immediately cooled and concentrated in vacuo. The residue was taken up in MeOH and treated with Bio-Rad AG 1-X8 resin (hydroxide form) until pH 8. The product was filtered and concentrated in vacuo to give 0.12 g (64% yield) of 2-amino-4-fluoro-2,3-dihydro-1H-inden-1-ol, which was used without further purification for the subsequent reductive amination.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperatureThe solution was immediately cooled
  3. concentrationconcentrated in vacuo
  4. additiontreated with Bio-Rad AG
  5. filtrationThe product was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a53afb9021cf4245af1e1d4633ce11f0
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…