Phthalimide potassium salt → 2-((4-Fluorotetrahydro-2h-pyran-4-yl)methyl)isoindoline-1,3-dione

HRID 1518867Notes

Reaction equation

HRID 1518867 reaction equation
CS(O[CH2:6][C:7]1([F:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)(=O)=O.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O.C(OCC)(=O)C>[F:13][C:7]1([CH2:6][N:18]2[C:14](=[O:24])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17]2=[O:19])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 87279396(4-Fluorotetrahydro-2h-pyran-4-yl)methyl methanesulfonate

Product 1

HCID 671270062-((4-Fluorotetrahydro-2h-pyran-4-yl)methyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of EXAMPLE 409A (1.8 g) and potassium phthalimide (2.356 g) in N,N-dimethylformamide (30 mL) was heated at 150° C. overnight, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, concentrated and chromatographed on silica gel with 30% ethyl acetate in hexanes as eluent to give the product.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 30% ethyl acetate in hexanes as eluent
  6. customto give the product

Sources & evidence

ORD record
ord-0d6a4362a34647fdbaf9d09a1d78948b
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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