Phthalimide → HCID 90052072, compound

HRID 2284665Notes

Reaction equation

HRID 2284665 reaction equation
[F:1][C:2]([F:17])([F:16])[CH:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:4]O.[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:1][C:2]([F:17])([F:16])[CH:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:4][N:22]1[C:18](=[O:28])[C:19]2[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:21]1=[O:23]

Participants

9

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 90052087HCID 90052087, compound

Product 1

HCID 90052072HCID 90052072, compoundYield 80.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,3,3-trifluoro-2-((3-nitrophenyl)amino)propan-1-ol (C14, 171 mg), phthalimide (201 mg) and triphenylphosphine (305 mg) in tetrahydrofuran (7 mL), a 40% solution of diethyl azodicarboxylate in toluene (526 μL) was added under ice cooling, and the mixture was stirred at the same temperature for 40 minutes. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 70% hexane in ethyl acetate) to obtain 2-(3,3,3-trifluoro-2-((3-nitrophenyl)amino)propyl)isoindoline-1,3-dione (C15, 209 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 70% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-152be0aa6e6446e0818f3debc6e48888
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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