Acetic Acid → (1R)-1-(3-chlorophenyl)-2-(4-phenylcyclohexylamino) ethanol

HRID 1108774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108774
C(O)(=O)C.[NH2:5][CH2:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[OH:8].[C:16]1([CH:22]2[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>CO.O=[Pt]=O>[Cl:15][C:11]1[CH:10]=[C:9]([C@@H:7]([OH:8])[CH2:6][NH:5][CH:25]2[CH2:24][CH2:23][CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:27][CH2:26]2)[CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 786054-PhenylcyclohexanoneHCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 54333897(1R)-1-(3-chlorophenyl)-2-(4-phenylcyclohexylamino) ethanolAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Acetic acid (1 ml) and PtO2 (160 mg) were added to a solution of (R)-2-amino-1-(3-chlorophenyl) ethanol (600 mg) and 4-phenylcyclohexanone (610 mg) in methanol (30 ml), and hydrogen addition was carried out at room temperature. After consumption of the starting materials, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. Separation and purification by silica gel column chromatography (chloroform:methanol=30:1) gave 43 mg of (1R)-1-(3-chlorophenyl)-2-(4-phenylcyclohexylamino) ethanol (4.0% yield).

Aufarbeitung

  1. customwas carried out at room temperature
  2. customAfter consumption of the starting materials
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customSeparation and purification by silica gel column chromatography (chloroform:methanol=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-cdb50a1fc331486aa07540a408ab6f05
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06069176

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