Triethylamine → HCID 69899447, compound

HRID 1582388Notes

Reaction equation

HRID 1582388 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]([OH:16])=O)[CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:31][C@H:32]1[CH:37]2[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]2)[CH2:33]1.C(N(CC)CC)C>C1COCC1>[N:34]12[CH2:39][CH2:38][CH:37]([CH2:36][CH2:35]1)[C@H:32]([N:31]1[C:10](=[O:12])[CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][C:14]1=[O:16])[CH2:33]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 77606N-Benzylaminodiacetic acidHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 69899447HCID 69899447, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-benzyliminodiacetic acid (2.23 g, 10.0 mmol) in THF (30 mL) was added 1,1′-carbonylbis-1H-imidazole (3.57 g, 22.0 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was stirred at reflux temperature for 30 min (until the evolution of C02 gas ceased, giving a clear solution), then cooled to room temperature. To the resulting mixture was added a solution of (3S)-3-aminoquinuclidine dihydrochloride (2.00 g, 10.0 mmol) and triethylamine (3.06 mL, 22.0 mmol) in THF (10 mL) stirred at room temperature under nitrogen atmosphere for 30 min via a cannula. The combined reaction mixture was stirred under reflux for 24 h, then cooled to room temperature and quenched with H2O (10 mL). The organic layer was extracted with EtOAc (50×2 mL) and the combined organic layers were dried over MgSO4, concentrated in vacuo. The residue was purified by column chromatography (NH gel, 200-350 mesh, 150 g, EtOAc) to give a product (2.17 g, 69%) as a white solid.

Workup

  1. temperatureat reflux temperature for 30 min (until the evolution of C02 gas
  2. customgiving a clear solution),
  3. stirringstirred at room temperature under nitrogen atmosphere for 30 min via a cannula
  4. customThe combined reaction mixture
  5. stirringwas stirred
  6. temperatureunder reflux for 24 h
  7. temperaturecooled to room temperature
  8. customquenched with H2O (10 mL)
  9. extractionThe organic layer was extracted with EtOAc (50×2 mL)
  10. dry with materialthe combined organic layers were dried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (NH gel, 200-350 mesh, 150 g, EtOAc)

Sources & evidence

ORD record
ord-9508d2f41d1343e38fb2725fe2b9c09b
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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