HCID 86686569, compound → 4′-Fluorospiro[cyclobutane-1,3′-[3H]indol]-2′(1′H)-one

HRID 1528090Notes

Reaction equation

HRID 1528090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[C:11]1([C:15]([O:17]C)=O)[CH2:14][CH2:13][CH2:12]1>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:11]1([CH2:14][CH2:13][CH2:12]1)[C:15](=[O:17])[NH:8]2

Participants

4

Reactant 1

HCID 86686569HCID 86686569, compound

Product 1

HCID 866865714′-Fluorospiro[cyclobutane-1,3′-[3H]indol]-2′(1′H)-oneYield 97.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 1-(2-fluoro-6-nitrophenyl)cyclobutanecarboxylate (3.11 g) in acetic acid (60 mL) was added zinc (16.1 g), and the mixture was stirred overnight at room temperature. The zinc was removed by filtration, and the filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.30 g).

Workup

  1. customThe zinc was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-583c37fc649c4e0593a695c600aec3d2
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

Loading…