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

Participants

Reaction Steps

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.

Provenance & Evidence