Phthalimide → 2-(2-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-dione
Reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]1(=[O:44])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36](=[O:43])[NH:35]1.[F:45][C:46]([F:61])([F:60])[C:47]1[CH:52]=[CH:51][N:50]=[C:49]([CH2:53][CH:54]2[CH2:58][CH2:57][CH2:56][CH:55]2O)[CH:48]=1>C1COCC1>[F:61][C:46]([F:45])([F:60])[C:47]1[CH:52]=[CH:51][N:50]=[C:49]([CH2:53][CH:54]2[CH2:58][CH2:57][CH2:56][CH:55]2[N:35]2[C:36](=[O:43])[C:37]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:34]2=[O:44])[CH:48]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
DIAD (0.26 ml, 1.36 mmol) was added to a solution of triphenylphosphine (0.350 g, 1.34 mmol), 2,3-dihydro-1H-isoindole-1,3-dione (CAS number 136918-14-4; 0.197 g, 1.34 mmol) and 2-{[4-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol (Diastereomer 2) (0.252 g, 1.03 mmol) in THF (5 ml). The reaction was stirred at room temperature for 24 hours and then further triphenylphosphine (0.175 g, 0.69 mmol) and DIAD (0.130 ml, 0.69 mmol) was added. The reaction was stirred for 72 hours at room temperature and then concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) and then by column chromatography (basic silica, 0-100% ethyl acetate/petrol) to afford the title compound.
Workup
- stirringThe reaction was stirred for 72 hours at room temperature
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
Sources & evidence
- ORD record
- ord-e4f3732e7568499e9d4183c2a0cb29c2
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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