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

HRID 2168406Notes

Reaction equation

HRID 2168406 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-a196993c123b4042a628240448e82175
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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