1,4-Dioxane → 2-[cis-2-(4-Fluoro-phenyl)cyclopropyl]-isoindole-1,3-dione

HRID 1479154Notes

Reaction equation

HRID 1479154 reaction equation
[Na].S(N[N:13]=[CH:14][C:15]1C=CC=C[C:16]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)(C1C=CC(C)=CC=1)(=O)=O.C(N1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])=C.O1CCOCC1.CCOC(C)=O.CCCCCC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2].O.CCOC(C)=O>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C@H:16]2[CH2:15][C@H:14]2[N:13]2[C:34](=[O:35])[C:33]3[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:31]2=[O:40])=[CH:26][CH:25]=1

Participants

9

Reactant 4

HCID 312751,4-DioxaneHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 21226206Ethyl acetate hexaneHCID 1317365734-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt

Product 1

HCID 897608182-[cis-2-(4-Fluoro-phenyl)cyclopropyl]-isoindole-1,3-dioneYield 12%

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 152122Dirhodium tetraacetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt (1.57 g, 5 mmol), N-vinyl-phthalimide (2.59 g, 15 mmol), benzyltriethylammonium chloride (114 mg, 0.5 mmol), and rhodium acetate dimer (22 mg, 0.05 mmol) were stirred with dioxane (23 ml) to give a thick slurry. This was stirred overnight at room temperature. TIc (20% EtOAc/hexane) showed good conversion, so the mixture was shaken between EtOAc and water. The organic phase was dried with MgSO4 and evaporated to yield 3.8 g of a crude mixture. This was chromatographed on silica with EtOAc/hexane to yield 169 mg (12%) of 2-[cis-2-(4-fluoro-phenyl)cyclopropyl]-isoindole-1,3-dione

Workup

  1. customto give a thick slurry
  2. dry with materialThe organic phase was dried with MgSO4
  3. customevaporated
  4. customto yield 3.8 g of a crude mixture
  5. customThis was chromatographed on silica with EtOAc/hexane

Sources & evidence

ORD record
ord-edafe781e23f407a94d9f04ee2a717db
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

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