Morpholine → 4-((3-Bromofuran-2-yl)methyl)morpholine

HRID 2190253

Reaktionsgleichung

Reaktionsgleichung von HRID 2190253
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=O.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH2:7][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 33672713-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 710658694-((3-Bromofuran-2-yl)methyl)morpholineAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-bromofuran-2-carbaldehyde (500 mg, 2.85 mmol) and morpholine (0.5 mL, 5.71 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (1.2 g, 5.71 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (100 mL). The organic phase was washed with aqueous NaHCO3 and brine then dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2) to afford the sub-title compound (670 mg, 89%).

Aufarbeitung

  1. washThe organic phase was washed with aqueous NaHCO3 and brine
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-8401e681973a4acfa7612176c9813769
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324264B1

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