Tetrahydrofuran → tert-Butyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-1-carboxylate

HRID 1445350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445350
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]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31187N-CarbethoxyphthalimideHCID 12682914-Amino-1-Boc-piperidine

Produkt 1

HCID 12063837tert-Butyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-1-carboxylateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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-carboethoxyphthalimide 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.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with an aqueous saturated sodium bicarbonate solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. filtrationcrystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0c4f5b3c345a45269cf174c09de8663f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666869B2

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