StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dichloromethane → 1,2,3,3a,8,8a-Hexahydro-alpha-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, phenylethyl ester

HRID 1681636
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1681636
[O:1]=[C:2]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]1[N:18]([CH3:21])[CH2:19][CH2:20][C:11]21[CH3:22])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH4+].[Cl-].C(Cl)Cl>C1(CCO)C=CC=CC=1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[O:1]=[C:2]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]1[N:18]([CH3:21])[CH2:19][CH2:20][C:11]21[CH3:22])[C:3]([O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:14]=[CH:15][CH:16]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 867464181,2,3,3a,8,8a-Hexahydro-alpha-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester

Produkt 1

HCID 867464191,2,3,3a,8,8a-Hexahydro-alpha-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, phenylethyl esterAusbeute 151,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76524
Titanium tetraethoxide
Katalysator
HCID 60542-PhenylethanolLösungsmittel

Versuchsvorschrift

To a chilled (0° C.) solution of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester (0.76 g) in anhydrous phenylethyl alcohol (18.1 ml) was added titanium (IV) ethoxide (0.22 ml) via syringe under a nitrogen atmosphere. The solution was warmed to room temperature and heated to just under reflux for 3 hours. The solution was then cooled to 0° C. and saturated NH4Cl solution was added slowly until a precipitate formed. Methylene chloride (200 ml) was then added and the mixture extracted twice with 100 ml portions of saturated aqueous NH4Cl solution, twice with 100 ml of saturated aqueous NaHCO3 and once with 100 ml of brine. The organic extracts were dried (Na2SO4), filtered, and the solvent removed on the rotary evaporator. The phenylethyl alcohol was then removed by distillation under high vacuum. The resulting residue was purified using preparative HPLC (silica gel, 4% methanol in ethyl acetate as the loading solvent and eluent). The appropriate fractions were combined, and the solvent removed to yield 0.72 g of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, phenylethyl ester, as an oil.

Aufarbeitung

  1. temperatureheated to just
  2. temperatureunder reflux for 3 hours
  3. temperatureThe solution was then cooled to 0° C.
  4. customformed
  5. extractionthe mixture extracted twice with 100 ml portions of saturated aqueous NH4Cl solution, twice with 100 ml of saturated aqueous NaHCO3 and once with 100 ml of brine
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed on the rotary evaporator
  9. customThe phenylethyl alcohol was then removed by distillation under high vacuum
  10. customThe resulting residue was purified
  11. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-5c91810484764d6282f1228a2afa6f09
Quelldatensatz
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05173497

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion