Hydrochloric Acid → HCID 86729751, Verbindung

HRID 2272592

Reaktionsgleichung

Reaktionsgleichung von HRID 2272592
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].C[Al](C)C.[OH:21][C:22]1([CH3:29])[CH2:27][CH2:26][O:25][C:24](=[O:28])[CH2:23]1.Cl>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:24](=[O:28])[CH2:23][C:22]([OH:21])([CH3:29])[CH2:27][CH2:26][OH:25])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 85883-Amino-9-ethylcarbazoleHCID 10428(+-)-MevalonolactoneHCID 16682925Trimethylaluminum

Produkt 1

HCID 86729751HCID 86729751, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of 9-ethyl-9H-carbazol-3-amine (300 mg, 1.43 mmol) in toluene (4 mL) was added trimethylaluminium (1.8M in toluene solution, 1.189 mL, 2.14 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added a solution of 4-hydroxy-4-methyltetrahydro-2H-pyran-2-one (186 mg, 1.43 mmol) in toluene (4 mL) at room temperature, and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was cooled to 0° C., neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give N-(9-ethyl-9H-carbazol-3-yl)-3,5-dihydroxy-3-methylpentanamide (359 mg, 1.056 mmol, 74.0%) as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for 4 hr
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c4387e4ab56f497e9361dcd751b5d166
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120776B2

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