methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate → methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927920Notes

Reaction equation

HRID 927920 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:18]C(=O)C(C)(C)C)[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]>S(=O)(=O)(O)O.CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:18])[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86713286methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 86713285methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylateYield 77.4%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

Concentrated sulfuric acid (5 drops) was added to a solution of methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate (Intermediate 30, 0.15 g) in methanol (5 mL) and the solution was stirred and heated at reflux for 48 hours. After cooling, the mixture was evaporated to low volume and the residue was dissolved in ethyl acetate and carefully washed with saturated aqueous sodium bicarbonate solution. The organic layer was filtered through a phase separator and the filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (0.09 g) as a brown gum.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to low volume
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washcarefully washed with saturated aqueous sodium bicarbonate solution
  7. filtrationThe organic layer was filtered through a phase separator
  8. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f54dc18af68f404f882cf295af3eba88
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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