Sodium borohydride → HCID 14521578, Verbindung

HRID 617621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617621
[BH4-].[Na+].[C:3]([CH:7]1[C:13](=[O:14])[CH2:12][CH:11]2[O:15][CH:8]1[CH2:9][CH2:10]2)([O:5][CH3:6])=[O:4]>CO>[C:3]([CH:7]1[CH:13]([OH:14])[CH2:12][CH:11]2[O:15][CH:8]1[CH2:9][CH2:10]2)([O:5][CH3:6])=[O:4]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 14521576HCID 14521576, Verbindung

Produkt 1

HCID 14521578HCID 14521578, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (2.56 g, 67.7 mmol) was added to a solution of 2-carbomethoxy-8-oxabicyclo(3.2.1)octan-3-one, 3, (5.12 g, 27.8 mmol) in MeOH (100 mL) at -78° C. The reaction mixture was left at room temperature overnight. The solution was concentrated to dryness. The residue was dissolved in water (50 mL), and extracted with CH2Cl2 (100, 2×50 mL). The combined dried (MgSO4) extracts were concentrated to dryness (yield: 3.9 g). By repeated flash column chromatography four isomers were obtained from the residue (2.9 g). The major isomer was 2α-carbomethoxy-3α-hydroxy-8-oxabicyclo(3.2.1)octane (1.0 g, 26%). Some of the other isomers were isolated to be used in the following reactions but there were still mixed fractions. Other pure isomers obtained: 2β-carbomethoxy-3α-hydroxy-8-oxabicyclo(3.2.1)octane (28 mg), 2β-carbomethoxy-3β-hydroxy-8-oxabicyclo(3.2.1)octane (305 mg) and 2α-carbomethoxy-3β-hydroxy-8-oxabicyclo(3.2.1)octane (84 mg).

Aufarbeitung

  1. concentrationThe solution was concentrated to dryness
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. extractionextracted with CH2Cl2 (100, 2×50 mL)
  4. dry with materialThe combined dried (MgSO4) extracts
  5. concentrationwere concentrated to dryness (yield: 3.9 g)

Quellen und Nachweise

ORD-Eintrag
ord-7349924e2690482b8a3e4e02d50a52c7
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948933

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