3,4-dihydro-2H-pyran → (4S)-4-(2-oxotetrahydro-2H-pyran-4-yloxy)pyrrolidin-2-one

HRID 883169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883169
[OH:1][C@@H:2]1[CH2:6][NH:5][C:4](=[O:7])[CH2:3]1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S([O-])(=O)=[O:21])=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[O:21]=[C:13]1[CH2:12][CH:11]([O:1][C@@H:2]2[CH2:6][NH:5][C:4](=[O:7])[CH2:3]2)[CH2:10][CH2:9][O:8]1

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 1550842-Pyrrolidinone, 4-hydroxy-, (4S)-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 68495162(4S)-4-(2-oxotetrahydro-2H-pyran-4-yloxy)pyrrolidin-2-oneAusbeute 608,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-4-hydroxypyrrolidin-2-one (1.00 g, 9.89 mmol) in anhydrous dichloromethane (40 mL) was added 3,4-dihydro-2H-pyrane (1.35 mL, 14.84 mmol) and pyridinium p-toluenesulfonate (0.25 g, 0.99 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with diethyl ether (100 mL) and washed with brine (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford (4S)-4-(2-oxotetrahydro-2H-pyran-4-yloxy)pyrrolidin-2-one as a clear oil (1.20 g, 61%): 1H NMR (300 MHz, CDCl3) δ 6.60 (br s, 1H), 4.98-4.57 (m, 1H), 4.57-4.46 (m, 1H), 3.89-3.70 (m, 1H), 3.68-3.22 (m, 3H), 2.69-2.22 (m, 2H), 1.89-1.50 (m, 6H).

Aufarbeitung

  1. washwashed with brine (25 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-134ac9aab2a8478991f3ce260e0c9359
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236835B2

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