Tetrahydrofuran → tert-Butyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-1-carboxylate
Reaction equation
C(N(CC)CC)C.O1CCCC1.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C(N1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42])(OCC)=O>O>[C:23]([O:22][C:20]([N:17]1[CH2:16][CH2:15][CH:14]([N:13]2[C:36](=[O:37])[C:35]3[C:34](=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:33]2=[O:42])[CH2:19][CH2:18]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]Participants
6
Procedure
16.7 ml of triethylamine was added to 200 ml of a tetrahydrofuran solution containing 16 g of 4-amino-1-tert-butoxycarbonylpiperidine and 17.5 g of N-carboethoxy-phthalimide under ice-cooling, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was suspended in ether-hexane, and crystals were collected by filtration to obtain 25.7 g of 2-(1-tert-butoxycarbonyl-4-piperidyl)-isoindoline-1,3-dione.
Workup
- temperaturecooling
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe extract was washed with an aqueous saturated sodium bicarbonate solution, water and brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was removed under reduced pressure
- filtrationcrystals were collected by filtration
Sources & evidence
- ORD record
- ord-32c5ca57e908418d972663324be41570
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332487B2
Reaction notes
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