Sodium borohydride → 4-(1-Hydroxy-2,2-dimethyl propyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

HRID 265108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265108
[BH4-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:8]([C:17]#[N:18])=[C:9]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[N:10]=1)[CH2:4][CH3:5]>C(O)C.O1CCCC1>[OH:16][CH:11]([C:9]1[N:10]=[C:6]([CH2:3][CH2:4][CH3:5])[N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[N:35]=[N:34][N:33]=3)=[CH:24][CH:25]=2)[C:8]=1[C:17]#[N:18])[C:12]([CH3:15])([CH3:13])[CH3:14]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 217408232-Propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

Produkt 1

HCID 190362484-(1-Hydroxy-2,2-dimethyl propyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrileAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 108 mg of sodium borohydride in 20 ml of ethanol was added to a solution of 2.00 g of 2-propyl -4-pivaloyl-1-[4-[2-(trityltetrazol-5-yl)-phenyl]phenyl}methylimidazole-5-carbonitrile [prepared as described in step (a) above] in 40 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2.5 hours. An the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The syrupy residue was crystallized in a 1:4 by volume mixture of ethyl acetate and hexane, to give 1.93 g of the title compound as crystals, melting at 115°-117° C.

Aufarbeitung

  1. concentrationAn the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe syrupy residue was crystallized in a 1:4 by volume mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-cb6cf5e40a3240f185dec7bd47e19686
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646171

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