N-Hydroxyphthalimide → HCID 86694011, compound

HRID 1053405Notes

Reaction equation

HRID 1053405 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[CH3:13][N:14]1[C:22]2[CH:21]3[CH2:23][CH:18]([CH2:19][CH2:20]3)[C:17]=2[C:16]([CH2:24]O)=[N:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:13][N:14]1[C:22]2[CH:21]3[CH2:23][CH:18]([CH2:19][CH2:20]3)[C:17]=2[C:16]([CH2:24][O:1][N:2]2[C:10](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:12])=[N:15]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58521564HCID 58521564, compound

Product 1

HCID 86694011HCID 86694011, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-hydroxy-1H-isoindole-1,3(2H)-dione (4.10 g, 25.2 mmol), (1-methyl-4,5,6,7-tetrahydro-1H-4,7-methanoindazol-3-yl)methanol 147 (2.24 g, 12.6 mmol) and triphenylphosphine (6.59 g, 25.2 mmol) in THF (100 mL) was added DIAD (5.35 mL, 27.6 mmol) slowly at room temperature. The resulting mixture was stirred at room temperature overnight and concentrated to provide a residue, which was subjected to chromatography to give 148 (1.80 g, 62%) as a yellow solid.

Workup

  1. concentrationconcentrated
  2. customto provide a residue, which

Sources & evidence

ORD record
ord-94233953722441ed983a1745a7db38c8
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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