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Phenol → HCID 10222398, Verbindung

HRID 1582454
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1582454
[CH2:1]([N:8]1[CH2:24][CH2:23][C:12]2=[C:13]([CH2:20][CH2:21][OH:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1(O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([N:8]1[CH2:24][CH2:23][C:12]2=[C:13]([CH2:20][CH2:21][O:22][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10268002HCID 10268002, Verbindung

Produkt 1

HCID 10222398HCID 10222398, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

(Chart D, Step 3): A dry round bottom flask is charged with 2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanol (420 mg, 1.31 mmol), phenol (185.2 mg, 1.97 mmol), triphenylphosphine (413 mg, 1.57 mmol), and THF (12 mL, freshly distilled). After cooling the reaction to 0° C., diethylazodicarboxylate (DEAD) (0.248 mL, 1.57 mmol) is added dropwise via syringe. The ice bath is allowed to expire, and the reaction is stirred at ambient temperature for 18 hours. The reaction is quenched with 30% H2O2 (0.20 mL), diluted with ethyl ether and washed twice with 10% aq. NaHSO3. The organics are washed twice with aq. 1N NaOH, once with brine, dried with Na2SO4, filtered and concentrated to 1.08 g of a crude yellow solid. Purification of the crude using silica gel and 10% ethyl acetate in heptane as the eluent gives 392 mg (76%) of 3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a pale yellow oil. HRMS (FAB) calculated for C27H28N2O+H1 397.2280, found 397.2271.

Aufarbeitung

  1. distillationfreshly distilled)
  2. temperatureAfter cooling
  3. customthe reaction to 0° C.
  4. customThe reaction is quenched with 30% H2O2 (0.20 mL)
  5. additiondiluted with ethyl ether
  6. washwashed twice with 10% aq. NaHSO3
  7. washThe organics are washed twice with aq. 1N NaOH, once with brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to 1.08 g of a crude yellow solid
  11. customPurification of the crude

Quellen und Nachweise

ORD-Eintrag
ord-f06eae3902ad49d4be85bf7b34e56914
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06734301B2

Notizen zur Reaktion

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