Acetyl chloride → 4-Cyclopropyl-1,8-diethyl-2,3,4,9-tetrahydro-1H-carbazole-1-acetic Acid Methyl Ester

HRID 1380927

Reaktionsgleichung

Reaktionsgleichung von HRID 1380927
[C:1]([CH2:5][C:6]1([CH2:16][CH3:17])[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:14][CH2:13]2)[CH2:8][C:7]1=O)([O:3][CH3:4])=[O:2].[CH2:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26]N)[CH3:19].C(Cl)(C)=O>CO>[CH3:4][O:3][C:1](=[O:2])[CH2:5][C:6]1([CH2:16][CH3:17])[C:7]2[NH:26][C:21]3[C:22](=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:18][CH3:19])[C:8]=2[CH:9]([CH:12]2[CH2:14][CH2:13]2)[CH2:10][CH2:11]1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 2733210(2-Ethylphenyl)hydrazineHCID 136492422-Carbomethoxymethyl-2-ethyl-5-cyclopropylcyclohexanone

Produkt 1

HCID 136492434-Cyclopropyl-1,8-diethyl-2,3,4,9-tetrahydro-1H-carbazole-1-acetic Acid Methyl EsterAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The mixture of diastereomeric ketones (40 mmol, 9.52 g) prepared in Step (d) and 2-ethylphenylhydrazine (40 mmol, 5.45 g) were heated at reflux in 172 ml of MeOH for 60 hours, cooled to 0° C. and treated with 80 mmol (6.28 g, 5.7 ml) of AcCl. The reaction was refluxed an additional 45 minutes followed by removal of solvent in vacuo. Flash chromatography afforded 4.58 g (13.5 mmol, 34%) of orange oil containing a mixture of diastereomers.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureThe reaction was refluxed an additional 45 minutes
  3. customfollowed by removal of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-78203b2344ab48beb07987c856158a23
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04584312

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