Borane;tetrahydrofuran → Uniconazole

HRID 1165373

Reaktionsgleichung

Reaktionsgleichung von HRID 1165373
N[C@@H](CC(C)C)C(C1C=CC=CC=1)(C1C=CC=CC=1)O.B.O1CCCC1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[C:35](/[N:42]2[CH:46]=[N:45][CH:44]=[N:43]2)\[C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[C:35](/[N:42]2[CH:46]=[N:45][CH:44]=[N:43]2)\[CH:36]([OH:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 2723981Borane;tetrahydrofuranHCID 10913254(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-oneHCID 10945486(S)-(-)-2-Amino-4-methyl-1,1-diphenyl-1-pentanol

Produkt 1

HCID 6436604UniconazoleAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

In a nitrogen atmosphere, 3.5 ml of a chloroform solution containing 0.233 g (0.86 mmole) of (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol was added at -60° C. to 0.87 ml (0.87 mmole) of a 1.0M borane-tetrahydrofuran solution, and the temperature of the resulting solution was raised to room temperature over 2 hours. Thereafter, 2 ml of a chloroform solution containing 0.164 g (0.57 mmole) of (E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one was added to this solution at room temperature, and stirring was carried out for 24 hours. After-treatment was carried out in the same manner as in Example 1 to obtain 0.164 g of (+)-(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol. The conversion was 87.0%, and the composition of the product was: E-form alcohol, 97.3% and Z-form alcohol, 2.7%. The enantiomer ratio of the E-form alcohol was: (+)-isomer, 87.2% and (-)-isomer 12.8%.

Aufarbeitung

  1. additionwas added to this solution at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-dfa53f16c8074f0cb5904f31a9b1b0ab
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908455

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