N-Hydroxyphthalimide → 2-(1-(3-(Trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione
Reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]([F:32])([F:31])[C:15]1[CH:16]=[C:17]([S:21]([N:24]2[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.O[N:34]1[C:42](=[O:43])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]1=[O:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:32][C:14]([F:13])([F:31])[C:15]1[CH:16]=[C:17]([S:21]([N:24]2[CH2:25][CH2:26][CH:27]([O:30][N:34]3[C:42](=[O:43])[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:35]3=[O:44])[CH2:28][CH2:29]2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of diethyl azodicarboxylate (1.10 g, 6.32 mmol) in tetrahydrofuran (5 ml) was added dropwise to a mixture of 1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-ol (0.94 g, 3.04 mmol), 2-hydroxyisoindoline-1,3-dione (0.50 g, 3.07 mmol) and triphenylphosphine (1.65 g, 6.30 mmol) in tetrahydrofuran (10 ml) at 0° C. The reaction mixture was stirred at room temperature for 17 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 25/75) to give 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (1.02 g, 74%) as a white solid: LCMS: 455 [M+1]+.
Workup
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (ethyl acetate/petroleum ether: 25/75)
Sources & evidence
- ORD record
- ord-3c31476d3ae44c2390893e3db1223c7b
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518934B2
Reaction notes
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