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Triethylamine → HCID 11223319, Verbindung

HRID 1783650
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1783650
C(Cl)(=O)C(Cl)=O.[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Cl.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]2[CH2:26][C@H:27]3[NH:38][CH2:37][CH2:36][C@@:33]4([C:34]=2[CH:35]=1)[C@H:28]3[CH2:29][CH2:30][CH2:31][CH2:32]4.C(N(CC)CC)C>C1COCC1>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]2[CH2:26][C@H:27]3[N:38]([C:16]([C:12]4[CH:11]=[C:10]5[C:15](=[CH:14][CH:13]=4)[NH:7][CH:8]=[CH:9]5)=[O:18])[CH2:37][CH2:36][C@@:33]4([C:34]=2[CH:35]=1)[C@H:28]3[CH2:29][CH2:30][CH2:31][CH2:32]4
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 742801H-Indole-5-Carboxylic AcidHCID 115655693-Methoxymorphinan hydrochloride (nor-de xtromethorphan

Produkt 1

HCID 11223319HCID 11223319, VerbindungAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

Oxalyl chloride (15 ul, 0.14 mmol) at RT was added to a solution of indole-5-carboxylic acid (0.02 g, 0.12 mmol) in THF (1 ml). After stirring at RT for 10 h, the mixture was added THF (1 ml) followed by (+)-3-methoxy-morphinan hydrochloride (0.04 g, 0.12 mmol), then triethylamine (0.1 ml, 0.7 mmol) was added and stirred for 18 h. The reaction mixture was filtered and washed with ethyl acetate. The filtrate was washed with saturated Na2CO3 (5 ml), dried (Na2SO4), filtered and concentrated at reduced pressure to give a crude pale brown oil. The crude product was purified by column chromatographed eluting with (MeOH:CH2Cl2=1:10) to give a pale yellow oil (0.013 g, 28% yield).

Aufarbeitung

  1. stirringstirred for 18 h
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with saturated Na2CO3 (5 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customto give a crude pale brown oil
  9. customThe crude product was purified by column
  10. customchromatographed
  11. washeluting with (MeOH:CH2Cl2=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-6d7d1b76c64b4f4bb2e305aa3f7ffb72
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07501433B2

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