Tryptophol → HCID 44224247, Verbindung

HRID 2066958

Reaktionsgleichung

Reaktionsgleichung von HRID 2066958
[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH:5]([CH3:10])[CH2:4]1.[CH:18]1[CH:19]=[CH:20][C:21]2[NH:26][CH:25]=[C:24]([CH2:27][CH2:28]O)[C:22]=2[CH:23]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl.C(O)C.O>[CH3:17][N:2]([CH3:1])[C:3]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][C:6]2([C:25]3[NH:26][C:21]4[C:22]([C:24]=3[CH2:27][CH2:28][O:9]2)=[CH:23][CH:18]=[CH:19][CH:20]=4)[CH:5]([CH3:10])[CH2:4]1

Komponenten

8

Edukt 4

HCID 10685TryptopholHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 67408596(+/-)-4-Dimethylamino-2-methyl-4-phenylcyclohexanone

Produkt 1

HCID 44224247HCID 44224247, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(±)-4-dimethylamino-2-methyl-4-phenylcyclohexanone (461 mg, 2 mmol) together with tryptophol (322 mg, 2 mmol) was dissolved in DCM (100 ml) and mixed with trifluoromethane sulphonic acid (0.19 ml, 2.14 mmol). The mixture was stirred at RT for 20 h. The reaction mixture was mixed with 2N NaOH (2 ml) and H2O (2 ml) and stirred for 20 min. The organic residue was firstly washed with 2N NaOH (5 ml), then with H2O (5 ml) and dried over Na2SO4. The solvent was then removed in vacuum. The semisolid residue obtained was taken up in 10 ml of ethanol and cooled to 5° C. for 2 h. The solid precipitated out during this was discarded. The residue remaining in the mother liquor was purified by column chromatography on silica gel (50 g, EE/ethanol=4:1).

Aufarbeitung

  1. stirringstirred for 20 min
  2. washThe organic residue was firstly washed with 2N NaOH (5 ml)
  3. dry with materialwith H2O (5 ml) and dried over Na2SO4
  4. customThe solvent was then removed in vacuum
  5. customThe semisolid residue obtained
  6. temperaturecooled to 5° C. for 2 h
  7. customThe solid precipitated out during
  8. customwas purified by column chromatography on silica gel (50 g, EE/ethanol=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ec71cc0884547ada054ee4e6bb528a7
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293758B2

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