N-Hydroxyphthalimide → HCID 67118434, compound

HRID 1895946Notes

Reaction equation

HRID 1895946 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]([C:22]2([N:25]3[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]3)[CH2:24][CH2:23]2)=[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:21]=[CH:20][C:19]([C:22]2([N:25]3[CH2:26][CH2:27][CH:28]([O:31][N:35]4[C:43](=[O:44])[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:36]4=[O:45])[CH2:29][CH2:30]3)[CH2:23][CH2:24]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67118486HCID 67118486, compound

Product 1

HCID 67118434HCID 67118434, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.23 ml, 2.70 mmol) was added dropwise to a solution of 1-(1-(4-(trifluoromethoxy)phenyl)cyclopropyl)piperidin-4-ol (750 mg, 2.45 mmol), 2-hydroxyisoindoline-1,3-dione (400 mg, 2.45 mmol) and triphenylphosphine (707 mg, 2.70 mmol) in tetrahydrofuran (15 ml) at 0° C. and the whole was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexane: 25/75 to 45/55) to give 2-(1-(1-(4-(trifluoromethoxy)phenyl)cyclopropyl)piperidin-4-yloxy)isoindoline-1,3-dione (1.00 g, 85%) as pale yellow amourphous.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (ethyl acetate/hexane: 25/75 to 45/55)

Sources & evidence

ORD record
ord-cdcc19f3c963410681e083dbe50457e1
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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