N-Hydroxyphthalimide → HCID 86694011, compound

HRID 330983Notes

Reaction equation

HRID 330983 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-5b478149413a4dc3a9fcf15548f705c0
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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