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

HRID 1040415Notes

Reaction equation

HRID 1040415 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[NH:17][C:16](=[O:18])[O:15][N:14]=2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C1(S)C=CC=CC=1>C(O)(C(F)(F)F)=O>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[NH:17][C:16](=[O:18])[O:15][N:14]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7969ThiophenolHCID 136383477(R)-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 136383470(R)-3-pyrrolidin-3-yl-4H-1,2,4-oxadiazol-5-oneYield 91.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe residue was partitioned between CH2Cl2 and water
  3. customThe layers were separated
  4. extractionthe CH2Cl2 layer was extracted with water
  5. concentrationThe combined aqueous layers were concentrated in vacuo
  6. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-13e92986632d44e498977bc5e7910043
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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