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

HRID 706920Notes

Reaction equation

HRID 706920 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 138A (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 eluting with 30% ethyl acetate in hexanes 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 eluting with 30% ethyl acetate in hexanes
  6. customto give the product

Sources & evidence

ORD record
ord-2aee11d46ef243a8a5a9333aeb05e05e
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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