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Hydrochloric Acid → methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

HRID 1905064
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1905064
[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH:10]([C:22]([O:24][CH3:25])=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29]O1.Cl.[OH-].[NH4+]>Cl.CO.O.CCOCC.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH:9]2[CH:30]([CH2:31][CH2:32][CH2:27][OH:26])[CH2:29][C:10]([C:22]([O:24][CH3:25])=[O:23])=[C:11]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19]23[CH2:20][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 1365052-HydroxytetrahydropyranHCID 11024114Azepino[4,5-B]indole-5-carboxylic acid,1,2,3,4,5,6-hexahydro-3-(phenylmethyl)-,methyl ester

Produkt 1

HCID 13856926methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 313Hydrochloric AcidKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5-carboxylate (1.336 g, 4.0 mmol), 2-hydroxytetrahydropyran (0.980 g, 8.2 mmol), toluene (30 mL) and ether saturated with HCl gas (10 drops) was heated under a nitrogen atmosphere at 110° C. for 5 h. The reaction mixture was cooled, diluted with 15 mL of methanol and acidified with conc. hydrochloric acid. The reaction mixture was stirred for 12 h at 20° C., poured into 50 mL of water and made strongly basic with ammonium hydroxide. The toluene layer was separated and the aqueous portion extracted three times with 25 mL of dichloromethane. The combined organic solutions were washed three times with 25 mL of saturated brine, dried over sodium sulfate and concentrated at 50° C. under vacuum to provide 1.67 g (100%) of methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylate, identical in spectroscopic properties and TLC Rf value to the product obtained in Example 1.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customThe toluene layer was separated
  3. extractionthe aqueous portion extracted three times with 25 mL of dichloromethane
  4. washThe combined organic solutions were washed three times with 25 mL of saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at 50° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d2165c8dbe0f4da0b7248038b46147f5
Quelldatensatz
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04841045

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