N-Hydroxyphthalimide → HCID 67118409, compound

HRID 1895908Notes

Reaction equation

HRID 1895908 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:43](=[O:44])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]1=[O:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[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:43](=[O:44])[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][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 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (8.86 g, 33.8 mmol) was added to a solution of 1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-ol (10.0 g, 30.7 mmol), 2-hydroxyisoindoline-1,3-dione (5.01 g, 30.7 mmol) and triphenylphosphine (8.86 g, 33.8 mmol) in tetrahydrofuran (100 ml) at 0° C. The reaction mixture was stirred at room temperature for 17 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 33/67) to give 2-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (11.6 g, 80%) as a white solid: LCMS: 471 [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (ethyl acetate/petroleum ether: 33/67)

Sources & evidence

ORD record
ord-e3d1471669d54685b740fef09bb784a4
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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