4-Methylmorpholine → HCID 178418271, Verbindung

HRID 3661

Reaktionsgleichung

Reaktionsgleichung von HRID 3661
[C:1]1([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CC[O:19]CC1.ClC(OCC(C)C)=O.C(N1[C:40]([NH2:41])=[C:39]([NH2:42])[C:37](=[O:38])N(CC=C)C1=O)C=C>O1CCCC1.C(OCC)C>[C:1]1([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:1]([CH:7]1[C:11](=[O:19])[CH:10]([CH2:9][CH:8]=[CH2:12])[C:37](=[O:38])[C:39]([NH-:42])=[C:40]1[NH2:41])[CH:2]=[CH2:3]

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 135250621,3-Diallyl-5,6-diaminouracilHCID 22884010trans-2-Phenyl-cyclopentanecarboxylic acid

Produkt 2

HCID 22884010trans-2-Phenyl-cyclopentanecarboxylic acidHCID 178418271HCID 178418271, VerbindungAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve trans-2-phenyl-cyclopentanecarboxylic acid (1.0 g, 5.3 mmol), prepared according to F. G. Bordwell and J. Almy, J. Org. Chem., 38, 571 (1973), in tetrahydrofuran (20 ml) and add N-methylmorpholine (0.58 ml, 5.3 mmol). Cool the reaction to -20° C. and add isobutyl chloroformate (0.69 ml, 5.3 mmol). Stir the reaction for 30 minutes, add 1,3-diallyl-5,6-diaminouracil (1.2 g, 5.3 mmol, in 4 ml dimethylformamide) and stir at -20° C. for 3 hours. Warm to room temperature and dilute the reaction with diethyl ether (400 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (2×200 ml), 50% aqueous sodium chloride (2×300 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by radial chromatography (2% to 5% methanol/chloroform, 2 mm plate) to provide trans-2-phenyl-cyclo-pentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enylamide (0.51 g).

Aufarbeitung

  1. customprepared
  2. temperatureCool
  3. customthe reaction to -20° C.
  4. customthe reaction for 30 minutes
  5. stirringstir at -20° C. for 3 hours
  6. additiondilute
  7. customSeparate the layers
  8. washrinse the organic layer with saturated sodium bicarbonate (2×200 ml), 50% aqueous sodium chloride (2×300 ml)
  9. dry with materialdry over anhydrous magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate under vacuum
  12. customPurify the residue by radial chromatography (2% to 5% methanol/chloroform, 2 mm plate)

Quellen und Nachweise

ORD-Eintrag
ord-ee021fa8c0fc47e48b1fbf4ceb821807
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05734052

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