Trifluoroacetic acid → HCID 68559167, compound

HRID 383900Notes

Reaction equation

HRID 383900 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH2:14][CH2:13][CH2:12][C:11]=13)[N:8](C(OC(C)(C)C)=O)[C:7]([CH3:23])([CH3:22])[C:6](=[O:24])[C:5]2([CH3:26])[CH3:25].FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH2:14][CH2:13][CH2:12][C:11]=13)[NH:8][C:7]([CH3:22])([CH3:23])[C:6](=[O:24])[C:5]2([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59233339HCID 59233339, compound

Product 1

HCID 68559167HCID 68559167, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-bromo-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (1.0 g) obtained in Example 1, 8) in CH2Cl2 (10 ml) was added trifluoroacetic acid (10 ml), and the mixture was stirred at room temperature for 1 hr. The reaction solution was neutralized with 1N aqueous sodium hydroxide solution, and the mixture was extracted with CHCl3. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane→hexane-ethyl acetate=7:3) to give the title compound (760 mg, 100%).

Workup

  1. extractionthe mixture was extracted with CHCl3
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washThe residue was subjected to normal phase chromatography (elution solvent hexane→hexane-ethyl acetate=7:3)

Sources & evidence

ORD record
ord-e7c9e1874e33474a8fb197079748fff0
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Reaction notes

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