Isoindoline → 2-(1,3-Dihydroisoindol-2-yl)-1-(1,4-dioxaspiro[4.5]dec-8-yl)ethanol

HRID 2063734Notes

Reaction equation

HRID 2063734 reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][NH:15]1.FC(F)(F)S([O-])(=O)=O.[Ca+2].FC(F)(F)S([O-])(=O)=O>C(#N)C>[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][N:15]1[CH2:3][CH:2]([CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[OH:1]

Participants

5

Reactant 3

HCID 422478IsoindolineHCID 2734307Methanesulfonic acid, 1,1,1-trifluoro-, calcium salt (2:1)HCID 585624888-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 668872712-(1,3-Dihydroisoindol-2-yl)-1-(1,4-dioxaspiro[4.5]dec-8-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 8-oxiranyl-1,4-dioxaspiro[4.5]decane (1.41 g, 7.66 mmol), isoindoline (1.00 g, 8.43 mmol) and calcium trifluoromethanesulfonate (1.29 g, 3.8 mmol) in anhydrous acetonitrile (60 ml) was stirred at room temperature overnight. The solvent was then concentrated in vacuo. The residue was taken up in ethyl acetate (50 ml) and the solution was washed with 25% potassium carbonate solution (3×50 ml). The aqueous phase was extracted with ethyl acetate (3×40 ml) and the combined organic phases were dried with sodium sulfate and concentrated in vacuo.

Workup

  1. concentrationThe solvent was then concentrated in vacuo
  2. washthe solution was washed with 25% potassium carbonate solution (3×50 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×40 ml)
  4. dry with materialthe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63af93fb11f947348e3285ee61a4e4f9
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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