Ethyl Acetate → HCID 58123735, compound

HRID 536681Notes

Reaction equation

HRID 536681 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH3:5][O:6][C:7]([C:9]1([CH2:19][CH2:20][CH2:21]Br)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]1=O)=[O:8].C(OC)(C)(C)C.C(OCC)(=O)C>CN(C)C=O>[CH3:5][O:6][C:7]([C:9]12[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11][CH:10]1[NH:1][CH2:21][CH2:20][CH2:19]2)=[O:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15413tert-Butyl methyl etherHCID 33557Sodium AzideHCID 58123513HCID 58123513, compound

Product 1

HCID 58123735HCID 58123735, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaN3 (0.44 g) is added to a solution of 1-(3-bromo-propyl)-2-oxo-indan-1-carboxylic acid methyl ester (2.06 g) in dimethylformamide (10 mL) at room temperature. The solution is stirred at room temperature for 4 h and then tBuOMe and ethyl acetate are added. The resulting mixture is washed with water and brine and dried (MgSO4). Most of the organic solvent is evaporated and tetrahydrofuran (10 mL), acetic acid (0.5 mL), and finally 10% Pd/C (150 mg) are added to the residue. The resulting mixture is shaken in hydrogen atmosphere (1 bar) at room temperature for 14 h. Then, the mixture is filtered, the filtrate is concentrated, and the residue is taken up in tBuOMe. The organic phase is washed with aqueous Na2CO3 solution and brine and dried (MgSO4). Then, the solvent is evaporated and the residue is dissolved in methanol (10 mL). To the solution is added acetic acid (0.5 mL) and 10% Pd/C (50 mg) and the resulting mixture is shaken under hydrogen atmosphere (1 bar) at room temperature for 6 h. Then, the mixture is filtered and the filtrate is concentrated under reduced pressure to give the crude title compound that is used without further purification.

Workup

  1. washThe resulting mixture is washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customMost of the organic solvent is evaporated
  4. additiontetrahydrofuran (10 mL), acetic acid (0.5 mL), and finally 10% Pd/C (150 mg) are added to the residue
  5. stirringThe resulting mixture is shaken in hydrogen atmosphere (1 bar) at room temperature for 14 h
  6. filtrationThen, the mixture is filtered
  7. concentrationthe filtrate is concentrated
  8. washThe organic phase is washed with aqueous Na2CO3 solution and brine
  9. dry with materialdried (MgSO4)
  10. customThen, the solvent is evaporated
  11. dissolutionthe residue is dissolved in methanol (10 mL)
  12. additionTo the solution is added acetic acid (0.5 mL) and 10% Pd/C (50 mg)
  13. stirringthe resulting mixture is shaken under hydrogen atmosphere (1 bar) at room temperature for 6 h
  14. filtrationThen, the mixture is filtered
  15. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c99a3a2df408423b8f4efb6178bb4cd3
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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