Sodium hydride → (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one

HRID 539080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539080
O[C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:15])[O:10]C(C)(C)C.[H-].[Na+].[NH4+].[Cl-]>C1COCC1>[O:15]1[C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]2[NH:8][C:9]1=[O:10]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11333385tert-butyl ((1S,2R)-2-hydroxycyclohexyl)carbaMate

Produkt 1

HCID 10877202(3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-oneAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 5.34 mmol) in THF (40 mL) was added NaH (60%, 0.32 g, 8.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature overnight. Saturated aqueous NH4Cl solution was added to quench the reaction. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexanes, 2:1) to give (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one (0.50 g, 66%) as a white solid.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. customThe mixture was partitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (EtOAc/hexanes, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-73db86f2acf345ecbad25538a8909e25
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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