Trifluoroacetic acid → HCID 90389354, compound

HRID 1526538Notes

Reaction equation

HRID 1526538 reaction equation
[F:1][CH:2]([F:17])[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[CH3:16])[CH:8]2[CH:6]([CH2:7]2)[O:5][NH:4]1.FC(F)(F)C(O)=O>C(O)(=O)C.[Zn]>[NH2:4][C:3]([CH:8]1[CH2:7][CH:6]1[OH:5])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[CH3:16])[CH:2]([F:1])[F:17]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90389378HCID 90389378, compound

Product 1

HCID 90389354HCID 90389354, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(difluoromethyl)-4-(3-fluoro-2-methylphenyl)-2-oxa-3-azabicyclo[3.1.0]hexane (0.81 g, 3.33 mmol) in acetic acid, glacial (7.69 ml, 133 mmol) was added zinc (1.306 g, 19.98 mmol) portionwise at RT followed by trifluoroacetic acid (2.474 ml, 33.3 mmol). The reaction was stirred at RT for 1 hour. The reaction was filtered through a pad of celite and concentrated under vacuum. The residue was dissolved in iced water and the solution was basified by the addition of 5N NaOH to pH 12. The basic aqueous layer was back extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to dryness to afford the title compound 2-(1-amino-2,2-difluoro-1-(3-fluoro-2-methylphenyl)ethyl)cyclopropanol (0.61 g, 2.487 mmol, 74.7% yield). LC/MS (ESI+) m/z=246.1 (M+H).

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in iced water
  4. additionthe solution was basified by the addition of 5N NaOH to pH 12
  5. extractionThe basic aqueous layer was back extracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c30df3f811764d42a7fd43ee98a61527
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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