Triphenylphosphine → HCID 86686575, compound

HRID 1528093Notes

Reaction equation

HRID 1528093 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[NH:6]2.[CH:17]1(O)[CH2:20][CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O>[CH:17]1([N:6]2[C:7]3[C:3](=[C:2]([F:1])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=3)[C:4]([CH3:16])([CH3:15])[C:5]2=[O:14])[CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 76218CyclobutanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86686556HCID 86686556, compound

Product 1

HCID 86686575HCID 86686575, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoro-3,3-dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one (300 mg), cyclobutanol (0.136 mL) and triphenylphosphine (702 mg) in THF (15 mL) was added dropwise diethyl azocarboxylate (40% toluene solution, 1.48 mL) at 0° C., and the mixture was stirred for 5 hr under a nitrogen atmosphere. To the reaction mixture was added water at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, 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 (200 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ad44b2ff94f44b49a6cf2fba3bfb4117
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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