Trifluoroacetic acid → HCID 86681888, compound

HRID 2409336Notes

Reaction equation

HRID 2409336 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2N3N=CC=[C:13]3[N:12]=[CH:11][C:10]=2[C:18](OCC)=O)=[C:4](C)[CH:3]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][C:10]3([CH2:11][NH:12][CH2:13]3)[CH2:18]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71178932HCID 71178932, compound

Product 1

HCID 86681888HCID 86681888, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 6-(4-fluorophenyl)-2,6-diazaspiro[3,3]heptane-2-carboxylate (0.029 g, 0.098 mmol) obtained in step 1 was dissolved in dichloromethane (0.3 mL), and trifluoroacetic acid (0.11 mL, 1.467 mmol) was added. The mixture was stirred at room temperature for 5 hr, and saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (0.013 g, 68%).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb608999ad74434b8dc19fdf0ee9ff62
Source dataset
uspto-grants-2014_08
Patent number
US08815874B2

Reaction notes

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