Trifluoroacetic acid → HCID 86761610, compound

HRID 2383046Notes

Reaction equation

HRID 2383046 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.CO[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH2:17][CH2:18][NH2:19].[C:23](OC(=O)C)(=[O:25])C.FC(F)(F)[C:32](O)=[O:33]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(O)=O>[CH3:32][O:33][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]21[C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:14]=1)[CH2:17][CH2:18][N:19]2[CH:23]=[O:25]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 107241-TetraloneHCID 748663-Methoxyphenethylamine

Product 1

HCID 86761610HCID 86761610, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tetralone (1.50 g), 3-methoxyphenethylamine (1.86 g), and titanium tetraisopropoxide (4.55 mL) was stirred under an argon atmosphere at 80° C. for 1 hour. The reaction mixture was cooled in an ice-MeOH bath. A mixture of formic acid (39 mL) and acetic anhydride (97 mL) was added to the reaction mixture under stirring at an internal temperature of 0° C. or lower. After the addition was complete, the reaction mixture was stirred at 80° C. for 2 hours, and trifluoroacetic acid (158 mL) was added thereto, followed by stirring at an internal temperature of 70° C. for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was made weak alkaline by using a saturated aqueous sodium hydrogen carbonate solution and was extracted with EtOAc. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 6 methoxy-3,3′,4,4′-tetrahydro-2H,2′H-spiro[isoquinoline-1,1′-naphthalene]-2-carbaldehyde (1.86 g).

Workup

  1. temperatureThe reaction mixture was cooled in an ice-MeOH bath
  2. additionwas added to the reaction mixture
  3. stirringunder stirring at an internal temperature of 0° C.
  4. additionAfter the addition
  5. stirringthe reaction mixture was stirred at 80° C. for 2 hours
  6. stirringby stirring at an internal temperature of 70° C. for 3 hours
  7. temperaturethe mixture was cooled to room temperature
  8. concentrationconcentrated under reduced pressure
  9. extractionwas extracted with EtOAc
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-dd7447ec8828440da7fe717ef91901b6
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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