Hydrochloric Acid → HCID 13869403, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1R,2S)-2-aminocyclopentanol (1.0 g, 9.9 mmol) as the HCl salt in water (50 mL) was added potassium hydroxide (3.9 g, 69 mmol) and the slurry stirred until all the material was in solute ion. To the reaction was added THF (100 mL) and the reaction was cooled to 0° C., followed by bis(trichloromethyl) carbonate (2.9 g, 9.9 mmol) as a solid and the reaction stirred at 0° C. for 2 hours. The reaction was poured into EtOAc and the layers were separated. The organic layer was washed with 1N HCl, 1N NaOH and brine, dried over MgSO4 and concentrated in vacuo. The material was purified by silica gel chromatography using 20% EtOAc/DCM as the eluent to yield (3aS,6aR)-hexahydro-2H-cyclopenta[d]oxazol-2-one (0.30 g, 2.4 mmol, 24% yield).

Provenance & Evidence