Phthalimide → 2-(2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1750479Notes

Reaction equation

HRID 1750479 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]1(=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[NH:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:45][C:46]([F:61])([F:60])[C:47]1[CH:48]=[CH:49][C:50]([CH2:53][CH:54]2[CH2:58][CH2:57][CH2:56][CH:55]2O)=[N:51][CH:52]=1>C1COCC1>[F:61][C:46]([F:45])([F:60])[C:47]1[CH:48]=[CH:49][C:50]([CH2:53][CH:54]2[CH2:58][CH2:57][CH2:56][CH:55]2[N:16]2[C:17](=[O:24])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]2=[O:25])=[N:51][CH:52]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 1183080932-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol

Product 1

HCID 1183081432-(2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (0.348 mL, 1.791 mmol) was added to a solution of 2,3-dihydro-1H-isoindole-1,3-dione (CAS number 136918-14-4; 0.263 g, 1.791 mmol), triphenylphosphine (0.470 g, 1.791 mmol) and 2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol (Diastereomer 2) (0.366 g, 1.492 mmol) in THF (2 ml) under nitrogen. The reaction was stirred at room temperature for 72 hours and then concentrated. The crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol) to afford the title compound.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-fd7ab422e65942439cb795afd51aa6ae
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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