Dichloromethane → (R)-3-pyrrolidin-3-yl-4H-1,2,4-oxadiazol-5-one

Participants

Reaction Steps

Crude (R)-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (872 mg, 3.41 mmol), CH2Cl2 (5 mL) and thiophenol (0.7 mL, 6.8 mmol) were combined and diluted with TFA (5 mL). After 24 h, the reaction was concentrated in vacuo. The residue was partitioned between CH2Cl2 and water. The layers were separated and the CH2Cl2 layer was extracted with water. The combined aqueous layers were concentrated in vacuo. Reverse phase HPLC purification yielded 482 mg of (R)-3-pyrrolidin-3-yl-4H-1,2,4-oxadiazol-5-one as a tan oil (˜50% pure) that was used without further purification.

Provenance & Evidence