Sodium Hydroxide → (1-Benzylazepan-3-yl)methanol

HRID 602119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602119
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:15](OC)=[O:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21902024Methyl 1-benzyl-2-oxoazepane-3-carboxylate

Produkt 1

HCID 21901990(1-Benzylazepan-3-yl)methanolAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 1-benzyl-2-oxoperhydroazepine-3-carboxylate (2.39 g, 9.15 mmol) was dissolved in tetrahydrofuran (50 mL). To this solution, lithium aluminum hydride (868 mg, 18.3 mmol) was added and the mixture was stirred for 2 hours while being refluxed. Subsequently, ice water and a 10% aqueous sodium hydroxide solution were added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then filtered through Celite. The filtrate was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) hexane:ethyl acetate=20:1->3:1) gave 1.30 g (65%) of the desired compound as a colorless oil.

Aufarbeitung

  1. temperaturewhile being refluxed
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationThe reaction mixture was then filtered through Celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe extract washed with brine
  6. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  7. customPurification of the residue by silica gel column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) hexane:ethyl acetate=20:1->3:1)

Quellen und Nachweise

ORD-Eintrag
ord-eb20ca407dc54af8a77dbf84661d7ebf
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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