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

HRID 539080Notes

Reaction equation

HRID 539080 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 10877202(3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-oneYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-73db86f2acf345ecbad25538a8909e25
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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