Water → [4-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)phenyl]methanol

HRID 32247

Reaktionsgleichung

Reaktionsgleichung von HRID 32247
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]2)=[C:12]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:27]2)[CH:11]=1.[F-].[Na+].O>O1CCCC1>[C:22]([CH:19]1[CH2:18][CH2:17][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]=2[N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:27]2)[CH2:21][CH2:20]1)([CH3:25])([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 587677084-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzoic acid methyl ester

Produkt 1

HCID 23142118[4-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)phenyl]methanolAusbeute 102,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (29 mg, 0.764 mmol) was suspended in anhydrous tetrahydrofuran (5 mL). To the suspension was added a solution of 4-(4-t-butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzoic acid methyl ester (308 mg, 0.743 mmol) in anhydrous tetrahydrofuran (5 mL) at room temperature under a nitrogen atmosphere, followed by stirring for 55 minutes. Sodium fluoride (262 mg) was added to the reaction mixture, and water (0.11 mL) was gradually added while blowing nitrogen. After stirring for 1 hour and 35 minutes, insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and anhydrous sodium sulfate was added for drying. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to give 295 mg of a crude product of the title compound as a colorless oil.

Aufarbeitung

  1. additionwas gradually added
  2. stirringAfter stirring for 1 hour and 35 minutes
  3. filtrationinsoluble materials were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in ethyl acetate
  6. additionanhydrous sodium sulfate was added
  7. customfor drying
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd39cbd617e54880bbc0e3a87968386c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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