Water → Triapenthenol

HRID 1383079

Reaktionsgleichung

Reaktionsgleichung von HRID 1383079
B([O-])=O.[Na+].[CH:5]1([CH:11]=[C:12]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O>O1CCCC1>[CH:5]1(/[CH:11]=[C:12](/[N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)\[CH:13]([OH:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 145326Sodium metaborateHCID 566097071-Cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one

Produkt 1

HCID 6437842Triapenthenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.68 g (0.018 mol) of sodium boranate is added to a suspension of 5.2 g (0.018 mol) of S-2-(dibenzyl-hydroxymethyl)-pyrrolidine hydrochloride in 75 ml of absolute tetrahydrofuran at -30° C., with stirring. The temperature is allowed to rise gradually to 20° C. and stirring is continued at 20° C. for a further 2 hours. Thereafter, 3.15 g (0.012 mol) of the (E)-isomer of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one are added dropwise and the mixture is stirred at 40° C. for 20 hours. The reaction mixture is then poured into water. The resulting mixture is extracted with ethyl acetate and the combined organic phases are concentrated uner reduced pressure. The residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel. 2.1 g (67% of theory) of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene are obtained on this manner in the form of a crystalline product.

Aufarbeitung

  1. customto rise gradually to 20° C.
  2. stirringstirring
  3. stirringthe mixture is stirred at 40° C. for 20 hours
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. concentrationthe combined organic phases are concentrated uner reduced pressure
  6. customThe residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6c1ba379364c49cbbd8f87cbc1c49e43
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808725

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