Ammonium Chloride → 2-(3-Hydroxy-3-phenylcyclopentyl)isoindoline-1,3-dione

HRID 2404388Notes

Reaction equation

HRID 2404388 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:3]1.[C:18]1([Mg]Cl)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[OH:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH:4]([N:7]2[C:8](=[O:17])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]2=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 545940982-(3-Oxocyclopentyl)-1H-isoindole-1,3(2H)-dioneHCID 178478979HCID 178478979, compound

Product 1

HCID 683134682-(3-Hydroxy-3-phenylcyclopentyl)isoindoline-1,3-dioneYield 27.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 58A (1.00 g, 4.36 mmol) and THF (20 mL) was cooled to <−70° C. and phenylmagnesium chloride (2.40 mL, 4.80 mmol) was added at <−70° C. After 2 hours, saturated aqueous NH4Cl (20 mL) was added and the mixture was extracted with MTBE (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was puridifed by flash column chromatography (0-20% EtOAc/hexanes, gradient elution), to provide the title compound (370 mg, 1.20 mmol, 27.6% yield).

Workup

  1. extractionthe mixture was extracted with MTBE (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. washThe residue was puridifed by flash column chromatography (0-20% EtOAc/hexanes, gradient elution)

Sources & evidence

ORD record
ord-416efc8c255f4724a5974a214fcec78e
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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