Sodium Hydroxide → HCID 68952905, Verbindung

HRID 539396

Reaktionsgleichung

Reaktionsgleichung von HRID 539396
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH3:18][C:19]1[CH:23]=[CH:22][S:21][C:20]=1[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.CN(C)C=O>[CH3:18][C:19]1[CH:23]=[CH:22][S:21][C:20]=1[CH2:24][N:8]1[CH2:7][CH2:6][C:5]2([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]2)[CH2:10][CH2:9]1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 799113-Methyl-2-thiophenecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Produkt 1

HCID 68952905HCID 68952905, VerbindungAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21926011acetic acid N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a 1% acetic acid-dimethylformamide (10 mL) solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (1.28 g) and 3-methylthiophene-2-carbaldehyde (700 mg), sodium triacetoxyborohydride (1.96 g) was added. The reaction solution was stirred at room temperature for 15 hours. To the reaction solution, an aqueous 5N sodium hydroxide solution (10 mL) was added. The aqueous layer was washed twice with dichloromethane (100 mL) The combined organic layer was washed with saturated sodium chloride solution (50 mL) and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1→1:3) to obtain the title compound (1.14 g) having the following physical properties.

Aufarbeitung

  1. washThe aqueous layer was washed twice with dichloromethane (100 mL) The combined organic layer
  2. washwas washed with saturated sodium chloride solution (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1→1:3)

Quellen und Nachweise

ORD-Eintrag
ord-91c554556952439db2106a03bef9a055
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871210B2

Verknüpfte Notizen

Wird geladen…