Water → (2S,3R,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol

HRID 2191044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191044
[CH2:1]([O:8][CH2:9][C@H:10]1[O:15][C@H:14]([O:16][CH3:17])[C@@H:13]2[C@@H:11]1[O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:18].[Na+].O>C(O)CO>[CH2:1]([O:8][CH2:9][C@H:10]1[O:15][C@H:14]([O:16][CH3:17])[C@@H:13]([OH:12])[C@@H:11]1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 5235Sodium FluorideHCID 86641125HCID 86641125, Verbindung

Produkt 1

HCID 11780118(2S,3R,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-olAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Compound 35.7 (2.2 g, 9.32 mmol) was dissolved in 10 mL ethyleneglycol, and then treated with NaF (2.2 g), KHF2 (2.2 g). The mixture was stirred at 200° C. for 4 h, cooled to r.t. and then treated with water (150 mL). The aqueous mixture was extracted twice with 200 mL EtOAc. The organic extracts were combined, dried over MgSO4, filtered and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 20-100% EtOAc in hexane to give compound 35.8 (786 mg, 33% yield).

Aufarbeitung

  1. temperaturecooled to r.t.
  2. extractionThe aqueous mixture was extracted twice with 200 mL EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down under reduced pressure
  6. washeluting with 20-100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-20c1a4c8c9ed4e1398160e656d798f82
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324179B2

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