N-Hydroxyphthalimide → HCID 67118409, compound

HRID 1044829Notes

Reaction equation

HRID 1044829 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]([F:33])([F:32])[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O[N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:33][C:14]([F:13])([F:32])[O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([N:25]2[CH2:26][CH2:27][CH:28]([O:31][N:35]3[C:39](=[O:40])[C:38]4[C:37](=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:36]3=[O:45])[CH2:29][CH2:30]2)(=[O:23])=[O:24])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 43394335HCID 43394335, compound

Product 1

HCID 67118409HCID 67118409, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (40% in toluene, 1.0 ml, 2.2 mmol) was added to the mixture of 1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-ol (651 mg, 2.0 mmol), N-hydroxyphthalimide (359 mg, 2.2 mmol) and triphenylphosphine (577 mg, 2.2 mmol) in THF (8 ml) at 0° C. and stirred at room temperature for 2 days. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica (EtOAc/Hexanes 10/90-50/50) to give 2-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (390 mg, 40%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography on silica (EtOAc/Hexanes 10/90-50/50)

Sources & evidence

ORD record
ord-12957dfd2af340d6b1f0ab09c35041b0
Source dataset
uspto-grants-2013_10
Patent number
US08563732B2

Reaction notes

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