Potassium Carbonate → HCID 58465644, compound

HRID 1842451Notes

Reaction equation

HRID 1842451 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]1[C:17]([O:19]CC)=O)=[N+]=[N-].C(=O)([O-])[O-].[K+].[K+]>CCO.C(Cl)Cl.Cl.[Pd]>[O:19]=[C:17]1[NH:1][CH2:4][CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]12

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 57517458HCID 57517458, compound2×

Product 1

HCID 58465644HCID 58465644, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-(3-azidopropyl)-1H-pyrrole-2,4-dicarboxylate Intermediate 7 (8 g, 27.2 mmol) in EtOH (800 mL) was added 10% Pd/C (2 g). The reaction was stirred at rt under a 30 psi H2 atmosphere for 2 h then filtered. To the filtrate was added potassium carbonate (4 g, 28.9 mmol). The reaction was then refluxed overnight. All the solids were then removed by filtration and the filtrate was then concentrated to give a solid which was dissolved in DCM (200 mL) and 1N aqueous HCl. After separation, the aqueous layer was extracted with DCM (2×150 mL). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to give ethyl 1-oxo-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxylate (4 g, 66%). 1H NMR (DMSO-d6, 300 MHz) δ7.88 (s, 1 H), 7.61 (s, 1 H), 6.84 (s, 1 H), 4.19 (m, 4 H), 3.09 (m, 2 H), 1.99 (m, 2 H), 1.25 (t, J=7.1 Hz, 3 H).

Workup

  1. filtrationthen filtered
  2. temperatureThe reaction was then refluxed overnight
  3. customAll the solids were then removed by filtration
  4. concentrationthe filtrate was then concentrated
  5. customto give a solid which
  6. customAfter separation
  7. extractionthe aqueous layer was extracted with DCM (2×150 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e1679cc7335e4333ae0374be5271f093
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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