Hydrochloric Acid → Triapenthenol

HRID 1165376

Reaktionsgleichung

Reaktionsgleichung von HRID 1165376
Cl.N[C@@H](CC(C)C)C(C1C=CC=CC=1)(C1C=CC=CC=1)O.[BH4-].[Na+].[CH:24]1(/[CH:30]=[C:31](/[N:38]2[CH:42]=[N:41][CH:40]=[N:39]2)\[C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl>ClCCCl.CN(C)C=O>[CH:24]1(/[CH:30]=[C:31](/[N:38]2[CH:42]=[N:41][CH:40]=[N:39]2)\[CH:32]([OH:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 12763477(E)-1-cyclohexyl-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-oneHCID 13036360(S)-2-amino-1,1-diphenyl4-methylpentan-1-ol hydrochloride

Produkt 1

HCID 6437842TriapenthenolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

In a nitrogen atmosphere, 0.275 g (0.90 mmole) of (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol hydrochloride was suspended in 5 ml of 1,2-dichloroethane, and after cooling to -20° C., a solution of 0.034 g (0.90 mmole) of sodium borohydride in 0.5 ml of dimethylformamide was added. The temperature of the suspension was then raised from -20° C. to room temperature over 2 hours. Thereafter, a solution of 157 mg (0.60 mmole) of (E)-1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one in 2 ml of 1,2-dichloroethane was added dropwise to this suspension at room temperature, and stirring was carried out for 24 hours. To this reaction solution was added 6 ml of 2N hydrochloric acid, and after removing liberated (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol hydrochloride by filtration, the organic layer was washed with water and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 0.158 g of (-)-(E)-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol. The conversion was 93.7%, and the composition of the product was: E-form alcohol, 95.7% and Z-form alcohol, 4.3%. The enantiomer ratio of the E-form alcohol was: (+)-isomer, 18.8% and (-)-isomer, 81.2%.

Aufarbeitung

  1. temperatureThe temperature of the suspension was then raised from -20° C. to room temperature over 2 hours
  2. customafter removing liberated (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol hydrochloride
  3. filtrationby filtration
  4. washthe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d5ad35a7830d4cbdb1a3b32a30730a5b
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908455

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