Potassium Carbonate → HCID 86642413, compound

HRID 1645339Notes

Reaction equation

HRID 1645339 reaction equation
C([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)=[O:7])(C)(C)C.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:13][C@H:10]2[CH2:11][CH2:12][N:8]([C:6]([OH:5])=[O:7])[CH2:9]2)=[N:16][CH:17]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 86642413HCID 86642413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-aminopyrrolidine-1-carboxylic acid-tert-butyl ester (5 g, 26.88 mmol) and 2-chloro-5-nitropyridine (4.26 g, 26.88 mmol) in THF (100 mL) was added potassium carbonate (7.42 g, 53.76 mmol). The mixture was refluxed for 72 hrs. The mixture was filtered and the filtrate was concentrated. The residue was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The oily residue was diluted with ether (50 mL) to give a clear solution which was kept at room temperature for 48 hrs. The crystalline material was filtered to give (S)-3-(5-nitro-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid test-butyl ester (6.66 g, 80.5% yield). LCMS for C14H20N4O4 calcd (m/e) 308, obsd 307 (M−H).

Workup

  1. temperatureThe mixture was refluxed for 72 hrs
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. extractionThe residue was extracted with ethyl acetate and water
  5. dry with materialThe organic layer was dried over sodium sulfate and solvents
  6. customwere evaporated
  7. additionThe oily residue was diluted with ether (50 mL)
  8. customto give a clear solution which
  9. filtrationThe crystalline material was filtered

Sources & evidence

ORD record
ord-17d7b6a365af437183ff139888593b42
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

Loading…